Stages of the formation and development of bioorganic chemistry. Bioorganic chemistry
Plan 1. Subject and value of bioorganic chemistry 2. Classification and range of organic compounds 3. Ways to image of organic molecules 4. Chemical bio bio organic Molecules 5. Electronic effects. The mutual influence of atoms in the molecule 6. Classification chemical reactions and reagents 7. The concept of chemical reaction mechanisms 2
The object of bioorganic chemistry 3 bioorganic chemistry. Independent section of chemical science, which studies the structure, properties and biological functions of chemical compounds of organic origin, which take part in the exchange of substances of living organisms.
Investigations of the study of bioorganic chemistry are low molecular weight biomolecules and biopolymers (proteins, nucleic acids and polysaccharides), biores-guides (enzymes, hormones, vitamins and others), natural and synthetic physiologically active compounds, including drugs and substances with toxic effect. Biomolecules - bioorganic compounds that are part of living organisms and specialized for the formation of cellular structures and participation in biochemical reactions form the basis of metabolism (metabolism) and physiological functions of living cells and multicellular organisms as a whole. 4 Classification of bioorganic compounds
The metabolism is a set of chemical reactions that flow in the body (in vivo). The metabolism is also called metabolism. Metabolism can occur in two directions - anabolism and catabolism. Anabolism is a synthesis in the body of complex substances from relatively simple. It occurs with the cost of energy (endothermic process). Catabolism - on the contrary, the decay of complex organic compounds to the simpler. It passes with the release of energy (exothermic process). Metabolic processes are held with the participation of enzymes. F E R E N T S is performed in the body the role of bio catalysts. Without enzymes, biochemical processes would not take place at all, or would have been hung very slowly and the body could not support life. five
Bioelements. The composition of bioorganic compounds, in addition to carbon atoms (C), which constitute the basis of any organic molecule, also includes hydrogen (H), oxygen (o), nitrogen (N), phosphorus (P) and sulfur (S). These bio-elements (organogen) are concentrated in living organisms in quantity that over 200 times the content in the objects of inanimate nature. The marked elements are over 99% of the elemental composition of the biomolecules. 6.
Bioorganic chemistry arose from the depths of organic chemistry and is based on its ideas and methods. In the history of development, such steps are assigned to organic chemistry: empirical, analytical, structural and modern. The period from the first acquaintance of a person with organic substances to the end of the XVIII century is considered empirical. The main result of this period - people realized the meaning of elemental analysis and the establishment of atomic and molecular masses. The theory of vitalism - vitality (Burtsellius). Until the 60s of the XIX century, analytical period continued. It was marked by the fact that from the end of the first quarter of the XX century, a number of promising discoveries were made, which caused a crushing blow to the vitalistic theory. The first in this row was a student of Burterus, German Chemik Veller. He carried out a number of discoveries in 1824 - Synthesis of oxalic acid from Ditiana: (CN) 2 Noos - Soton R. - Synthesis of urea from ammonium cyanate: NH 4 CNO NH 2 - C - NH 2 O 8
In 1853 Sh. Gerard developed the "Type Theory" and also used it for the classification of organic compounds. According to Gerarr, more complex organic compounds can be produced from the following major four types of substances: NNN Type of hydrogen NNNN O Type of water N Cl Type of hydrogen chloride NNHNH N Type Ammonia from 1857 At the proposal of F. A. Kekule, hydrocarbons began to attribute to the type of methane nnhnnhan nine
The main provisions of the structure of the structure of organic compounds (1861) 1) atoms in molecules are connected to each other chemical bonds in accordance with their valence; 2) atoms in organic substance molecules are connected in a certain sequence, which causes the chemical structure (structure) of the molecule; 3) the properties of organic compounds depend not only on the number and nature of the atoms included in their composition, but also on the chemical structure of molecules; 4) In organic molecules, there is interaction between atoms, both associated with each other and unrelated; 5) The chemical structure of the substance can be determined as a result of the study of its chemical transformations and, on the contrary, it is possible to characterize its properties on the structure of the substance. 10
The main provisions of the structure of the structure of organic compounds (1861) structural formula is an image of the flow sequence of atoms in the molecule. Gross formula - CH 4 O or CH 3 OH Structural formula Simplified structure formulas are sometimes called rational molecular formula - an organic compound formula that indicates the number of atoms of each element in the molecule. For example: C 5 H 12 - Pentan, from 6 H 6 - gasoline, etc. eleven
The development of bioorganic chemistry as a separate area of \u200b\u200bknowledge, which combines the conceptual principles and the methodology of organic chemistry on one side and molecular biochemistry and molecular pharmacology on the other hand, bioorganic chemistry was formed in the years of the twentieth century on the basis of the development of chemistry of natural substances and biopolymers. The fundamental importance of modern bioorganic chemistry has acquired thanks to the works of V. Stein, S. Mura, F. Senger (analysis of the amino acid composition and the definition of the primary structure of peptides and proteins), L. Poling and H. Astbury (clarification of the structure - Spiral and-structure and their meaning In the sale of biological functions of protein molecules), E. Chargaff (deciphering the peculiarities of the nucleotide composition of nucleic acids), J. Watson, FR. Creek, M. Wilkins, R. Franklin (establishment of patterns of the spatial structure of the DNA molecule), Karta (chemical synthesis of gene), etc. fourteen
Classification of organic compounds on the structure of the carbon skeleton and nature of the functional group The huge number of organic compounds prompted chemists to conduct their classification. The classification of organic compounds is based on two classification features: 1. The structure of the carbon skeleton 2. The nature of functional groups Classification according to the method of the structure of the carbon skeleton: 1. acyclic (alkanes, alkenes, alkina, alkadium); 2. Cyclic 2.1. Carbocyclic (alicyclic and aromatic) 2.2. Heterocyclic 15 acyclic compounds are also called aliphatic. They own substances with an impected carbon chain. Acyclic compounds are divided into saturated (or limit) with N H 2N + 2 (alkanes, paraffins) and unsaturated (unforeseen). The latter include alkenes with n h 2n, alkina with N H 2N -2, alkadena with N H 2N -2.
16 Cyclic compounds in the composition of their molecules contain rings (cycles). If the cycles include only carbon atoms, then such compounds are called carbocyclic. In turn, carbocyclic compounds are divided into alicyclic and aromatic. The alicyclic hydrocarbons (cycloalkanes) includes cyclopropane and its homologues - cyclobutane, cyclopentane, cyclohexane, and so on. If the cyclic system except the hydrocarbon includes other elements, then such compounds refer to heterocyclic.
The classification of the nature of the functional group The functional group is an atom or a group of certainly related atoms, the presence of which in the organic substance molecule determines the characteristic properties and its belonging to a particular compound class. In terms of the number and homogeneity of functional groups, organic compounds are divided into mono-, poly and heterofunctional. The substances with one functional group are called monofunctional, with several identical functional groups with polyfunctional. Compounds containing several different functional groups of hetero functional. It is important that the compounds of the same class are combined into homologous series. Homological series These are a number of organic compounds with the same functional groups and the same type, each representative of the homologous series differs from the previous one on a permanent unit (CH 2), which is called homologous difference. The members of the homologous series are called homologists. 17.
Nomenclature systems in organic chemistry - trivial, rational and international (IUPAC) Chemical nomenclature The set of names of individual chemicals, their groups and classes, as well as the rules for compiling their names. Chemical nomenclature The set of names of individual chemicals, their groups and classes, as well as rules compiling their names. Trivial (historical) nomenclature is associated with the process of obtaining substances (pyrogallol - the product of pyrolysis of gallic acid), the source of origin from which (formic acid) was obtained, etc. The trivial titles of the compounds are widely used in the chemistry of natural and heterocyclic compounds (citral, geraniol, thiophen, pyrrol, quinoline, etc.). Trivial (historical) nomenclature is associated with the process of obtaining substances (pyrogallol - gallic acid pyrolysis product), source of origin, from which was obtained (formic acid), etc. The trivial titles of the compounds are widely used in the chemistry of natural and heterocyclic compounds (citral, geraniol, thiophene, pyrrole, quinoline, etc.). The basis of the rational nomenclature uses the principle of dividing organic compounds into homologous series. All substances in a certain homologous series are considered as derivatives of the most simple representative of this series - the first or sometimes second. In particular, alkanov - methane, in alkens - ethylene, etc. The basis of the rational nomenclature is used by the principle of dividing organic compounds into homologous series. All substances in a certain homologous series are considered as derivatives of the most simple representative of this series - the first or sometimes second. In particular, Alkanov - methane, in alkenes - ethylene, etc. eighteen
International Nomenclature (IUPAC). The rules of modern nomenclature were developed in 1957 at the Congress of the International Union of Theoretical and Applied Chemistry (International Union of Pure and Applied Chemistry - IUPAC). Radical-functional nomenclature. The basis of these names is the name of the functional class (alcohol, ether, ketone, etc.), which is preceded by the names of hydrocarbon radicals, for example: alilchloride, diethyl ether, dimethyl ketone, propyl alcohol, etc. Replacement nomenclature. Rules of nomenclature. The general structure is a structural fragment of the molecule (molecular core) underlying the title of the compound, the main carbon chain of atoms for alicyclic compounds, for carbocyclic - cycle. nineteen
Chemical bond in organic molecules Chemical bond - phenomenon of the interaction of external electronic shells (fluctuation electrons of atoms) and atomic nuclei, which causes the existence of a molecule or crystal as a whole. As a rule, atom, taking, giving an electron or forming a common electronic pair, seeks to acquire a configuration of an external electron shell similar to inert gases. For organic compounds, the following types of chemical bonds are characterized: - ion connection -Connerable communication - DONOR - acceptor bond - Exchange, also have some other types chemical bond (metal, one-electron, two-electron three-center), but they practically do not occur in organic compounds. twenty
Types of ties in organic compounds most characteristic of organic compounds is a covalent connection. Covalent bond is the interaction of atoms that is implemented through the formation of a common electron pair. This type of communication is formed between atoms that have comparable electronegability values. Electricity - an atom property showing the ability to delay electrons from other atoms. Covalent bond can be polar or non-polar. Non-polar covalent bond arises between atoms with the same electronegability value
Types of bonds in organic compounds The covalent polar bond is formed between atoms that have different electronegability values. In this case, the associated atoms acquire partial charges δ + δ + δ-Δ- Special subtype covalent Communication It is a donor-acceptor connection. As in the previous examples, this type of interaction is due to the presence of a common electron pair, but the latter is provided by one of the atoms of the forming bond (donor) and is accepted by another atom (acceptor) 24
Types of bonds in organic compounds ionic communication is formed between atoms that are very different from electronegability values. In this case, the electron is less than the electronegative element (often it is metal) completely proceeds to a more electronegative element. This electron transition causes the appearance of a positive charge in a less electronegative atom and a negative in more electronegative. Thus, two ions are formed with the opposite charge, between which there is electrosal interaction. 25.
Types of bonds in organic compounds The hydrogen bond is electrostatic interaction between the hydrogen atom, which is bound by the strong-polar bond, and electron pairs of oxygen, fluorine, nitrogen, sulfur and chlorine. This type of interaction is rather weak interaction. Hydrogen bond can be intermolecular and intramolecular. Intermolecular hydrogen bond (interaction between two ethyl alcohol molecules) intramolecular hydrogen bond in Salicyl Aldehyde 26
Chemical bond in organic molecules The modern theory of chemical bond is based on a quantum-mechanical model of a molecule as a system consisting of electrons and atomic nuclei. The cornerstone concept of quantum-mechanical theory is atomic orbital. Atomic orbital is a part of the space in which the probability of finding electrons is maximum. Communication, therefore, can be considered as interaction ("overlapping") orbital, which carry one electron with opposite spins. 27.
The hybridization of atomic orbitals according to the quantum-mechanical theory, the amount of covalent bonds formed by an atom is determined by the amount of single-electron atomic orbitals (the number of unpaired electrons). At the carbon atom, there are only two unpaired electrons in the main state, but the possible transition of an electron with 2s to 2 PZ causes the possibility of forming four covalent bonds. The condition of the carbon atom, in which it has four unpaired electrons is called "excited". Despite the fact that carbon orbitals are unequal, it is known that the formation of four equivalent bonds due to the hybridization of atomic orbitals is possible. Hybridization - a phenomenon in which of several different in the form and energies for the energy of orbital is formed the same number of the same in the form and number of orbital. 28.
Hybrid states of carbon atom in organic molecules The first hybrid state of an atom with is in a state SP 3-hybridization forms four σ-bonds, forms four hybrid orbitals, which are located in the form of tetrahedra (valence angle) σ-Communication 31
The hybrid states of the carbon atom in organic molecules The second hybrid state of an atom C is in a state of SP 2-hybridization, forms three σ- bonds, forms three hybrid orbitals, which are located in the form of a flat triangle (valence angle 120) σ-bond π-communication 32
Hybrid states of carbon atom in organic molecules The third hybrid state atom C is in a state of SP-hybridization, forms two σ- connections, forms two hybrid orbitals, which are located in line (valence angle 180) σ-bond π-bonds 33
Characteristics of chemical bonds of the genuine scale: F-4.0; O - 3.5; Cl - 3.0; N - 3.0; Br - 2.8; S - 2.5; C-2.5; H-2.1. Difference 1.7.
Characteristics of chemical bonds The polarizability of the communication is the displacement of electron density under the action of external factors. Polarizability of communication is the degree of electron mobility. With an increase in the atomic radius, the polarizability of electrons will increase. Therefore, the polarizability of the carbon bond - halogen increases as follows: C-F 
Electronic effects. The mutual influence of atoms in the molecule 39 in modern theoretical representations, the reactivity of organic molecules is predetermined by the displacement and mobility of electronic clouds that form a covalent bond. In organic chemistry, two types of electron displacements are distinguished: a) electronic displacements occurring in the system - bonds, b) electronic displacements transmitted by the-bonding system. In the first case, there is a so-called inductive effect, in the second - mesomeric. The inductive effect is the redistribution of electron density (polarization) resulting from the difference in electronegativity between the atoms of the molecule in the - bonding system. After a minor polarizability, the inductance effect quickly fuses and after 3-4 communication it is almost no manifest.
Electronic effects. The mutual influence of atoms in a molecule 40 The concept of inductive effect was introduced by K. Ingold, they were also introduced notation: -i-effect in case of decrease by the electron density of the electron density + i-effect in the case of an increase in electron density. Positive inductive effects show alkyl radicals (CH 3, from 2 H 5 -, etc.). All other substituents associated with carbon atom show a negative inductive effect.
Electronic effects. The mutual influence of atoms in a molecule 41 mesomeric effect call the redistribution of electron density along the conjugate system. The conjugate systems belong to the organic compounds molecules, in which double and single connections alternate or when a double bond is placed next to a double bond, having an empty pair of electrons on a p-orbital. In the first case, there is a place - a pairing, and in the second - p, -sopher. The conjugate systems are with an open and closed pairing chain. An example of such compounds is 1,3-butadiene and gasoline. In the molecules of these compounds, carbon atoms are in a state of SP 2-hybridization and due to non-liberal p-orbitals form-devices, which mutually overlap together and form a single electronic cloud, that is, there is a pairing.
Electronic effects. The mutual influence of atoms in a molecule 42 There are two types of mesomeric effect - a positive mesomeric effect (+ m) and a negative mesomeric effect (s). A positive mesomeric effect is displayed by substituents providing p-electrons into a conjugate system. These include: -o, -s -Nn 2, -One, -or, Hal (halogens) and other substituents who have a negative charge or a molar pair of electrons. The negative mesomeric effect is characteristic of substituents delaying -electronic density from the conjugate system. These include substituents who have multiple links between atoms with different electronegitility: - N0 2; -SO 3 N; \u003e C \u003d O; -Son and others. The mesomeric effect is graphically reflected by a bent arrow, which shows the direction of displacement of the electrons in contrast to the induction effect, the mesomeric effect does not go out. It is transmitted completely through the system, regardless of the length of the conjugation chain. C \u003d O; -Son and others. The mesomeric effect is graphically reflected by a bent arrow, which shows the direction of displacement of the electrons in contrast to the induction effect, the mesomeric effect does not go out. It is passed entirely on the system, regardless of the length of the conjugation chain. "\u003e 
Types of chemical reactions 43 Chemical reactions can be considered as the interaction of the reagent and substrate. Depending on the method of breaking and forming a chemical bond in molecules, organic reactions They divide on: a) homolytic b) heterolithic c) molecular homolytic or free-radical reactions are due to a homologous tip of communication, when each atom remains one electron, that is, radicals are formed. The homolytic gap occurs at high temperatures, the action of the quantum of light or catalysis.
Heterolytic or ionic reactions occur in such a way that the pair of binding electrons remains about one of the atoms and ions are formed. The particle with the electronic pair is called nucleophist and has a negative charge (-). The particle without an electronic pair is called electrical and has a positive charge (+). 44 types of chemical reactions
The chemical reaction mechanism 45 by the reaction mechanism is called a set of elementary (ordinary) stages, of which this reaction consists. The reaction mechanism most often includes such steps: activation of the reagent to form the electrophila, nucleophile, or free radical. To activate the reagent, we need a catalyst. In the second stage, the activated reagent with the substrate occurs. In this case, intermediate particles (intermediates) are formed. The latter belongs to -complexes, -complexes (carboats), carbants, new free radicals. At the final stage, there is an attachment or cleavage of K (from) formed in the second stage by an intermediate of some particle with the formation of a final reaction product. If the reagent generates a nucleophile during activation, then it is nucleophilic reactions. They are marked with the letter N - (in the index). In the case when the reagent generates electrophile, the reaction belongs to the electrophilic (E). Similarly, it can be said about free radical reactions (R).
Nucleophiles - reagents having a negative charge or an atom-enriched atom: 1) Anions: OH -, CN -, RO -, RS -, HAL - and other anions; 2) neutral molecules with watered electron pairs: NH 3, NH 2 R, H 2 O, ROH and others; 3) Molecules with excess electron density (having - communications). Electrophilas - reagents with a positive charge or depleted electron atom: 1) Cations: H + (proton), NSO 3 + (ion hydrogen sulfonium), NO 2 + (ion nitrony), NO (nitrosonia ion) and other cations; 2) Neutral molecules having a vacant orbital: AlCl 3, FeBr 3, SNCl 4, BF 4 (Lewis acids), SO 3; 3) molecules with depleted electron density on the atom. 46.
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Lecture 1.
Bioorganic chemistry (BOH), its meaning in medicine
Boh is a science that studies the biological function of organic substances in the body.
Boh appeared in the 2nd half of the twentieth century. The objects of its study serve biopolymers, bioregulators and individual metabolites.
Biopolymers are high molecular weight natural compounds that are the basis of all organisms. These are peptides, proteins, polysaccharides, nucleic acids (NK), lipids, etc.
Bioregulators - compounds that chemically regulate the metabolism. These are vitamins, hormones, antibiotics, alkaloids, drugs, etc.
Knowledge of the structure and properties of biopolymers and bioregulators allows you to know the essence of biological processes. Thus, the establishment of the structure of proteins and the NK made it possible to develop the ideas about the matrix biosynthesis of protein and the role of the NK in the preservation and transmission of genetic information.
Boh plays a major role in establishing the mechanism of action of enzymes, drugs, processes, respiration, memory, nervous conductivity, muscular abbreviation, etc.
The main problem of Boh is the clarification of the relationship between the structure and the mechanism of the compounds.
Boh is based on organic chemistry material.
ORGANIC CHEMISTRY
This is a science that studies carbon compounds. Currently there are ~ 16 million organic substances.
Causes of the variety of organic substances.
1. Compounds of atoms with each other and other elements. periodic system D. Mendeleev. At the same time, chains and cycles are formed:
Straight chain branched chain
Tetrahedral flat configuration
the configuration of the atom from the atom with
2. Homology is the existence of substances with close properties, where every member of the homologous series differs from the previous group
-CH 2 -. For example, a homologous series of limiting hydrocarbons:
3. Isomerius is the existence of substances having the same quality and quantitative composition, but a different structure.
A.M. Butlers (1861) created the theory of the structure of organic compounds, which to this day serves as a scientific basis of organic chemistry.
The main provisions of the structure of the structure of organic compounds:
1) atoms in molecules are connected to each other chemical bonds in accordance with their valence;
2) atoms in organic compound molecules are connected in a certain sequence, which causes the chemical structure of the molecule;
3) the properties of organic compounds depend not only on the number and nature of the atoms included in their composition, but also on the chemical structure of molecules;
4) in molecules there is a mutual influence of atoms both related and non-associated with each other;
5) The chemical structure of the substance can be determined as a result of the study of its chemical transformations and, on the contrary, in the structure of the substance, it is possible to characterize its properties.
Consider some provisions of the theory of the structure of organic compounds.
Structural isomeria
She shares:
1) isomeria chain
2) Isomerization of the position of multiple communication and functional groups
3) Isomerius of functional groups (interclace isomerism)
Formulas Newman
Cyclohexane
The shape of the "chair" is more energetically beneficial than the "bath".
Configuration isomers
These are stereoisomers whose molecules have a different location of atoms in space excluding conformations.
By type of symmetry, all stereoisomers are divided into enantiomers and diastereomers.
Enantiomers (optical isomers, mirror isomers, antipodes) are stereoisomers whose molecules are among themselves as an object and an incompatible mirror image. This is the phenomenon of the Nazny Enantiomeria. All chemical and physical signs of enantiomers are the same, except for two: the rotation of the polarized light plane (in the polarimeter instrument) and biological activity. Enantiomeria conditions: 1) Atom C is in a state of SP 3-hybridization; 2) the absence of any symmetry; 3) the presence of an asymmetric (chiral) atom with, i.e. Atom having four Different deputy.
Many oxide and amino acids have the ability to rotate the polarization plane of the light beam left or right. This phenomenon is called optical activity, and the molecules themselves are optically active. The deviation of the beam of light to the right marks the "+" sign, left - "-" and indicate the angle of rotation in degrees.
The absolute configuration of molecules is determined by complex physico-chemical methods.
The relative configuration of optically active compounds is determined by comparison with the standard of glycerin aldehyde. Optically active things that have a configuration of the reprisal or left-hander glycerin aldehyde (M. Rozanov, 1906), the name of the thing D- and L-series. Equally, a mixture of the right and leaving isomers of one compound of the Naza-Xia racemate and optically inactive.
Studies have shown that the light rotation sign cannot be connected to the accessory of things to D- and L-rows, it is determined only experimentally in the instruments - polarimeters. For example, L-dairy K-TA has an angle of rotation +3.8 O, D- dairy K-TA - -3.8 o.
Enantiomers are depicted using Fisher's formulas.
L-row D-row
Among the enantiomers can be symmetric molecules that do not have optical activity, and called mesoisomers.
 |
| For example: Wine K-TA |
| D - (+) - Series L - (-) - Row | Meson |
Rakezate - grape k-ta
Optical isomers that are not mirror isomers, characterized by a configuration of several, but not all asymmetric atoms with various physical and chemicals, Naz-S- di-but-Steroisomers.
p-diastereomers (geometric isomers) are stereometers having a P-link molecule. They are found in alkenes, unsaturated higher carboxylic k-t, unsaturated dicarboxylic
The biological activity of organic things is associated with their structure.
For example:
Cis-buldic k-ta, trans-boatdiova k-ta,
malein K-Ta - Fumarov K-Ta - not poisonous,
very poison contained in the body
All natural unforeseen top carboxylices are cis-isomers.
Lecture 2.
Conjugated systems
In the simplest case, the conjugate systems are systems with alternating double and single connections. They can be open and closed. The open system is available in diene hydrocarbons (HC).
Examples:CH 2 \u003d CH - CH \u003d CH 2
Butadiene-1, 3
ChlorhetenCH 2 \u003d CH - SL
There is a pair of p-electrons with P-electrons. This type of interface is called P, P-pairing.
The closed system is available in aromatic uv.
From 6 H 6
Aromatic
This is a concept that includes various properties of aromatic compounds. Conditions of aromaticity: 1) Flat closed cycle, 2) All atoms with are in SP 2 - hybridization, 3) forms a single conjugate system of all cycle atoms, 4) The Hyukkel rule is performed: "4n + 2 p-electrons are involved in the conjugation, where N \u003d 1, 2, 3 ... "
The simplest representative of aromatic HC - benzene. It satisfies all four aromatic conditions.
Hyukkel rule: 4n + 2 \u003d 6, n \u003d 1.
Mutual influence of atoms in a molecule
In 1861, a Russian scientist A.M. Butlers expressed the position: "Atoms in molecules mutually influence each other." Currently, this effect is transmitted in two ways: inductive and mesomeric effects.
Inductive effect
This is the transfer of electronic influence on the s-communication circuit. It is known that the relationship between atoms with different electronegitability (EO) is polarized, i.e. shifted to more EO atom. This leads to the appearance of effective (real) charges atoms (D). Such an electronic shift is inductive and indicated by the letter I and the arrow ®.
, X \u003d nl -, but -, ns -, nn 2 - etc.
Inductive effect can be positive or negative. If the substituent attracts the electrons of the chemical bond is stronger than atom H, then it exhibits - I. i (H) \u003d O. In our example, X exhibits - I.
If the substituent attracts the electron of communication is weaker than atom H, then it exists + i. All alkyls (R \u003d CH 3 -, C 2 H 5 -, etc.), and N + exhibit + i.
Mesometer effect
The mesomeric effect (the effect of the conjugation) is the effect of the substituent transmitted by the conjugate system of P-links. Denotes the letter M and the curved arrow. The mesomeric effect may be "+" or "-".
Above it, it was said that there are two types of pairing p, p and p, p.
The substituent, attracting electrons from the conjugate system, exhibits -M and the Naz-Xia electron acceptor (EA). These are substituents who have a double
 |
communication and others.
The substituent, exhausing electrons in the conjugate system, exhibits + M and the Naz-XI electronone (ED). These are substituents with single connections having a watered electronic pair (etc.).
Table 1 Electronic effects of substituents
| Deputy | Orientants in from 6 N 5 -R | I. | M. |
| Olk (R-): CH 3 -, from 2N 5 -... | Orientants I kind: Direct Ed substituents in ortho- and para- | + | |
| - H 2, -NNR, -NR 2 | – | + | |
| - n, - n, - r | – | + | |
| - L. | – | + | |
|
Lecture 3. Acidity and basicity For the characteristics of the acidity and base base of organic compounds, the theory of Brenstead is used. The main provisions of this theory: 1) acid is a particle that gives proton (donor H +); The base is a particle accepting proton (H + acceptor). 2) Acidness is always characterized in the presence of bases and vice versa. A - n +: in û a - + in - n + aSN-IE K-TA CH 3 coxy + non-û CH 3 Soo - + H 3 O + K-TU OSN-IE conjugate conjugate aSN-IE K-TA NNO 3 + CH 3 sooh û CH 3 Soam 2 + + NO 3 - K-TU OSN-IE conjugate conjugate k-TA OSN-IE Brenstened acids 3) K-You Brensteads are divided into 4 species depending on the acid center: SN K-You (Tiol), He is to-you (alcohols, phenols, carbon k-you), Nn k-you (amines, amides), CH K-you (HC). In this row from top to bottom, acidity decreases. 4) The strength of the K-you is determined by the stability of the generated anion. The more stable anion, the stronger the most. The stability of anion depends on the delocalization (distribution) "-" charge across the entire particle (anion). The more delocalized the "-" charge, the more stable anion and stronger K-TA. Delocalization of charge depends: a) From electronegativity (EO) heteroatom. The larger the EO heteroatom, the stronger the corresponding K is. For example: R - it and R - NN 2 Alcohols are stronger to-you than amines, because EO (O)\u003e EO (N). b) from the polarizability of the heteroatom. The greater the polarizability of the heteroatom, the stronger the corresponding to-one. For example: R - SN and R - it Tiol is stronger to-you than alcohols, because Atom S is more polarized than O. c) on the nature of the substituent R (length of it, the presence of a conjugate system, elocalizing electron density). For example: CH 3 - it, CH 3 - CH 2 - it, CH 3 - CH 2 - CH 2 - He Acidity<, т.к. увеличивается длина радикала
CH 3 - it, from 6 H 5 - he, Strength k-you increase Phenols are stronger than the alcohols due to the p, p-pairing (+ m) of the group -one.
In addition, carboxylate-anion is more stable than alcohol anion due to P, P-pairing in the carboxyl group.
For example: r-nitrophenol is stronger k-ta than p-aminophenol, because Group -No 2 is EA. CH 3 SL 3-SCO rK 4.7 RK 0,65 Trichloroacetic K-Ta is many times stronger than CH 3 coxy due to - I atoms with CL as EA. The anti-ta n-coxy is stronger than CH 3 coxy due to + I group CH 3 - acetic to-you. e) on the nature of the solvent. If the solvent is a good proton acceptor N +, then Bases of Brenets 5) they are divided into: a) p-base (compounds with multiple connections); b) n-base (ammonium containing atom oxonium containing atom sulfonium containing atom) The base force is determined by the stability of the resulting cation. The more stable the cation, the stronger the base. In other words, the base force is the greater, the less durable connection with the heteroatom (o, S, N) having a free electronic pair attacked by H +. The stability of the cation depends on the same factors as the stability of the anion, but with reverse action. All factors reinforcing acidity reduce the basicity. The strongest bases are amines, because The nitrogen atom has a smaller EO compared to O. In this case, secondary amines are stronger bases than primary, tertiary amines are weaker secondary due to a steric factor that makes it difficult to access the proton to N.
Aromatic amines are weaker bases than aliphatic, which is explained by + M Group of 2. The electron pair of nitrogen, participating in the conjugation, becomes a larger. The stability of the conjugate system makes it difficult to attach H +. In the urea 2 -CH 2 there is an EA group\u003e C \u003d O, which significantly reduces the launched SV-VA and the urea forms a salt with only one equivalent to-you. Thus, the stronger the more, the weaker the base formed by it and vice versa. Alcohol These are derivatives of HC, in which one or more atoms n are replaced by a group. Classification: I. By the number of groups, it distinguishes monatomic, dioxide and polyhydric alcohols: CH 3-SN 2 -H Ethanol ethylene glycol glycerol
II. Accordingrica, R is distinguished by: 1) the limit, 2) unforeseen, 2) CH 2 \u003d CH-CH 2 -H Allyl alcohol
retinol (Vitamin A) and cholesterol
vitamin-like in-in |
With the same acid center, the strength of alcohols, phenols and carboxylices is not the same. For example,
The connection of the ON is more polarized in phenols. Phenols can interact even with salts (FES1 3) - high-quality reaction to phenols. Carbonic 
d) from the introduction of deputies to the radical. Ea substituents increase acidity, Ed substituents reduce acidity.
3) There are persistent cyclic alcohols:
InositIII. Under the provision of c. - It is distinguished by primary, secondary and tertiary alcohols.
IV. By the number of atoms with distinguished low molecular weight and high molecular weight.
CH 3 - (CH 2) 14 -CH 2 -One (from 16 H 33) CH 3 - (CH 2) 29 -CH 2 it (from 31N 63)
Cetyl alcohol Miricyl alcohol
Cetilpalmitat - the base of spermaceta, mycricillmitte is contained in the bee wax.
Nomenclature:
Trivial, rational, MN (root + End "Ol" + Arabic digit).
Isomeria:
chains, position c. -One, optical.
The structure of the alcohol molecule
Sn-acid nu center
Electrophilic center acid
center base center
Oxidation
1) alcohols are weak acids.
2) Alcohols - weak grounds. M + is attached only from strong acids, but they are stronger Nu.
3) -i effect c. "It increases the mobility of H in a neighboring carbon atom. Carbon acquires D + (electrophilic center, S E) and becomes the center of the nucleophilic attack (NU). Communication C-oh is more easily, than n-o, therefore, characteristic of alcohols, the yawls of the P-│ s n. They, as a rule, go in an acidic environment, because The protonation of the oxygen atom increases D + carbon atom and makes it easier to break the communication. This type includes the rations of the formation of ether, halogen production.
4) The displacement of the electronic density from H in the radical leads to the appearance of a CH-acid center. In this case, the rations of oxidation and elimination (E) go.
Physical SV-Wa
Lower alcohols (C 1 -C 12) - liquids, higher - solid. Many of the alcohols are explained by the formation of n-communications:
Chemical sv-va
I. Acid-focused
Pumps are weak amphoteric compounds.
2R-ON + 2NA ® 2R-ONA + H 2
Alcoholate
Alcohboles are easily hydrolyzed, which shows - alcohols weaker acids than water:
R- ONA + NON ® R-ON + NAON
Ensuring center in alcohols - heteroatom about:
CH 3 -CH 2 -One + H + ® CH 3 -CH 2 - -N ® CH 3 -CH 2 + + H 2 OIf the ration goes with halogen hydrogen, then the halide ion will be connected: CH 3 -CH 2 + + SL - ® CH 3 -CH 2 SL
NS1 RO \u200b\u200bR-SOM NN 3 C 6 H 5 ONA
C1 - R-O - R-SOO - NN 2 - C 6 N 5 O -
Anions in such rods act as nucleophiles (NU) due to the "-" charge or vulnerable electronic pair. Anions are stronger bases and nucleophilic reagents than alcohol themselves. Therefore, in practice, the alcoholates are used to obtain simple and esters, and not alcohol themselves. If the nucleophil is another alcohol molecule, it joins the carbocathion:
|
This is the ration of alkylation (the introduction of alkyl R in the molecule).
Replace -on gr. On halogen, under the action of RSl 3, PCl 5 and SOSL 2.
In such a mechanism, tertiary alcohols react easier.
P-Qi S E with respect to the alcohol molecule is the formation of esters of esters with organic and mineral tools:
R - O N + N O - R - O - + H 2 O
Ester
This is the № acylation - the introduction of acila to the molecule.
CH 3 -CH 2 -One + N + CH 3 -CH 2 - -n CH 3 -CH 2 +With an excess of H 2 SO 4 and a higher temperature than in the case of the formation of the formation of ethers, the catalyst regeneration is regenerated and alkene is formed:
CH 3 -CH 2 + + NSO 4 - ® CH 2 \u003d CH 2 + H 2 SO 4
It is easier for the R-│ E for tertiary alcohols, harder for secondary and primary, because In the last cases, less stable cations are formed. In these R-α, A. Zaitseva rule is performed: "With the dehydration of alcohols, atom H is cleaved from a neighboring atom with a lower content of N atoms.
CH 3 -CH \u003d CH -CN 3
Butanol-2.
In the body c. -One turns into an easy way to form ethers with H 3 PO 4:
CH 3 -CH 2 -On + N-PO 3 H 2 CH 3 -CH 2 ON 3N 2IV. Oxidation
1) Primary and secondary alcohols are oxidized by Cuo, KMNO 4 solutions, K 2 CR 2 O 7 when heated to the formation of appropriate carbonyl compounds:
Nitroglycerin is a colorless oil liquid. In the form of dilute alcohol solutions (1%) is used for angina, because It has a vasodilatory action. Nitroglycerin is a strong explosive that can explode from impact or when heated. At the same time in a small volume, which occupies a liquid substance, a very large volume of gases instantly is formed, which causes a strong explosive wave. Nitroglycerin is part of the dynamite, powder.
Representatives of pentates and hexides are xylitis and sorbitol - respectively, five- and six-coat alcohols with an open chain. The accumulation of the group leads to the appearance of a sweet taste. Xylitis and sorbitol - sugar substitutes for patients with diabetes.
Glizorophosphate - structural phospholipid fragments, are used as a lining agent.
Benzyl alcohol
Isomers of the Regulation
Chemistry- science on the structure, properties of substances, their transformations and accompanying phenomena.
Tasks:
1. Study of the structure of the substance, the development of the theory of the structure and properties of molecules and materials. It is important to establish a connection between the structure and various properties of substances and on this basis the construction of the theories of the reaction capacity of the substance, kinetics and the mechanism of chemical reactions and catalytic phenomena.
2. Implementation of the directional synthesis of new substances with specified properties. It is also important to find new reactions and catalysts for more effective implementation of the synthesis of already known and having industrial import value.
3. The traditional task of chemistry has gained special importance. It is associated both with an increase in the number of chemical objects and studied properties and the need to determine and reduce the effects of human impact on nature.
Chemistry is generalory discipline. It is designed to give students a modern scientific view of a substance as one of the types of moving matter, about the paths, mechanisms and methods of transforming one substances into others. Knowledge of basic chemical laws, ownership of chemical calculation techniques, an understanding of the possibilities provided by chemistry with the help of other specialists working in individual and narrow areas, significantly accelerates obtaining the necessary result in various areas of engineering and scientific activities.
The chemical industry is one of the most important industries in our country. Chemical compounds produced by it, various compositions and materials are used everywhere: in mechanical engineering, metallurgy, agriculture, construction, electrical and electronic industry, communications, transport, space technology, medicine, everyday life, etc. The main directions of development of the modern chemical industry are: production new compounds and materials and improving the efficiency of existing industries.
In a medical university, students explore common, bioorganic, biological chemistry, as well as clinical biochemistry. Knowledge of students complex chemical Sciences In their continuity and relationships, they give a greater opportunity, greater space in the study and practical use of various phenomena, properties and patterns, contributes to the development of the personality.
Specific features of studying chemical disciplines in medical university are:
· Interdependence between chemical and medical education purposes;
· Universality and fundamentality of these courses;
· Feature of building their content, depending on the nature and general objectives of the training of a doctor and its specialization;
· Unity of studying chemical objects on micro and macro levels with disclosure different shapes of their chemical organization as a single system and manifest themselves different functions (chemical, biological, biochemical, physiological, etc.) depending on their nature, medium and conditions;
· Dependence on the connection of chemical knowledge and skills with real reality and practice, including medical, in the Society - Nature - Manufacturing - Manufacturing system, due to the unlimited possibilities of chemistry in the creation of synthetic materials and their meaning in medicine, the development of nanochemistry, as well as in solving environmental and many others global problems mankind.
1. The relationship between the process of metabolism and energy in the body
The processes of life on Earth are due to a large extent with the accumulation of solar energy in biogenic substances - proteins, fats, carbohydrates and subsequent transformations of these substances in living organisms with energy release. Especially clearly understanding the relationship of chemical transformations and energy processes in the body was conscious after works A. Lavoisier (1743-1794) and P. Laplas (1749-1827). They show direct calorimetric measurements that the energy that is secreted in the process of life is determined by the oxidation of the food of the air, inhaled animals.
The metabolism and energy - a set of processes of transformation of substances and energy occurring in living organisms, and the metabolism and energy exchange between the body and environmental. The metabolism and energy is the basis of the vital activity of organisms and belongs to the number of most important specific signs of living matter, distinguishing living from non-living. In the exchange of substances, or metabolism provided by the most complex regulation at different levels, many enzyme systems are involved. In the process of exchange, the substances received in the body are converted into eigenous substances of the tissues and to the final products that are separated from the body. With these transformations, energy is released and absorbed.
With development in the XIX-XX centuries. Thermodynamics - sciences of mutual and energies and energies - it became possible to quantify the conversion of energy in biochemical reactions and predict their direction.
Energy exchange can be carried out by heat transfer or performance. However, living organisms are not in equilibrium with the environment and therefore may be called non-equilibrium open systems. However, when observed over a certain period of time, there is no visible changes in the chemical composition of the organism. But this does not mean that the chemicals constituting the body are not subjected to any transformations. On the contrary, they are constantly and rather intensively updated, as can be judged by the rate of inclusion in complex substances of stable isotopes and radionuclides introduced into the cell in the composition of simpler predecessor substances.
There is one between the exchange of substances and energy exchange fundamental difference. The land does not lose and does not receive any noticeable amount of substance. The substance in the biosphere exchanges on a closed cycle and that Used repeatedly. Energy exchange is carried out otherwise. It does not circulate along a closed cycle, but partly dissipated into the external space. Therefore, to maintain life on Earth, a constant inflow of the energy of the Sun is necessary. For 1 year in the process of photosynthesis on the globe absorbs about 10 21 cal.solar energy. Although it is only 0.02% of all the energy of the Sun, it is immeasurably greater than that energy that is used by all machines created by the hands of a person. As much as a large amount of substance participating in the circuit circuit.
2. Chemical thermodynamics as a theoretical basis of bioenergy. The subject and methods of chemical thermodynamics
Chemical thermodynamicshe is studying the transitions of chemical energy into other forms - thermal, electrical, etc., sets the quantitative laws of these transitions, as well as the direction and limits of spontaneous flow of chemical reactions under specified conditions.
The thermodynamic method is based on a number of strict concepts: "System", "System Condition", "Internal Energy System", "System State Function".
Object learning in thermodynamics is the system
The same system can be in different states. Each system status is characterized by a specific set of thermodynamic parameters. The thermodynamic parameters include temperature, pressure, density, concentration, etc. The change of at least one thermodynamic parameter leads to a change in the state of the system as a whole. The thermodynamic state of the system is called equilibrium if it is characterized by the constancy of thermodynamic parameters in all points of the system and does not change spontaneously (without cost).
Chemical thermodynamics examines the system in two equilibrium states (finite and initial) and on this basis determines the possibility (or inability) of the spontaneous flow of the process under specified conditions in the specified direction.
Thermodynamics learnthe mutual transformations of various types of energy associated with the transition of energy between the bodies in the form of heat and work. Thermodynamics is based on two basic laws that have received the name of the first and second principle of thermodynamics. Subject of study In thermodynamics is the energy and laws of mutual transformations of energy forms in chemical reactions, dissolution processes, evaporation, crystallization.
Chemical thermodynamics - section of physical chemistry studying the processes of the interaction of substances by thermodynamic methods.
The main directions of chemical thermodynamics are:
Classical chemical thermodynamics studying thermodynamic equilibrium at all.
Thermochemistry studying the thermal effects accompanying chemical reactions.
The theory of solutions that simulate thermodynamic properties of the substance based on the representations of the molecular structure and data on intermolecular interaction.
Chemical thermodynamics closely comes into contact with such sections of chemistry as analytical chemistry; electrochemistry; colloid chemistry; Adsorption and chromatography.
The development of chemical thermodynamics was at the same time in two ways: thermochemical and thermodynamic.
The emergence of thermochemistry as independent science should be considered the discovery of Hermann Ivanovich Hesse, the professor of the St. Petersburg University, the relationship between the thermal effects of chemical reactions --- the laws of the hess.
3. Thermodynamic systems: isolated, closed, open, homogeneous, heterogeneous. The concept of phase.
System - This is a combination of interacting substances, mentally or virtually separate from the environment (test tube, autoclave).
Chemical thermodynamics considers transitions from one state to another, it may change or remain constant some parameters:
· isobaric - at constant pressure;
· isochoric - at a constant volume;
· isothermal - at a constant temperature;
· isobaro - isothermal - at constant pressure and temperature, etc.
Thermodynamic properties of the system can be expressed using several system status functions, called characteristic features: internal energy , entalpy H. , entropy S. , energy Gibbs G. , energy Helmholts F. . Characteristic functions have one feature: they do not depend on the method (path) of achieving this system status. Their value is determined by the parameters of the system (pressure, temperature, etc.) and depends on the amount or mass of the substance, so it is customary to belong to one praying of the substance.
According to the method of transmission of energy, substance and information between the system under consideration and the environment, thermodynamic systems are classified:
1. Closed (isolated) system - This is a system in which there is no exchange with external bodies either with energy or substance (including radiation) nor information.
2. Closed system - The system in which there is an exchange for only energy.
3. Adiabato isolated system -this is a system in which there is an exchange of energy only in the form of heat.
4. Open system - This is a system that is exchanged with energy, and substance and information.
System classification:
1) If possible, heat and mass transfer: isolated, closed, open. The isolated system does not exchange with the environment or substance nor energy. The closed system exchanges with the environment, but not exchanged substance. The open system exchanges with the environment and substance and energy. The concept of an isolated system is used in physical chemistry as a theoretical.
2) on the internal structure and properties: homogeneous and heterogeneous. A homogeneous is called a system inside which there are no surfaces that divide the system on parts, various properties or chemical composition. Examples of homogeneous systems are aqueous solutions of acids, bases, salts; Gas mixtures; Individual pure substances. Heterogeneous systems contain natural surfaces inside. Examples of heterogeneous systems are systems consisting of various substances in the aggregative state: metal and acid, gas and solid substance, two insoluble in each other fluid.
Phase - this is a homogeneous part of the heterogeneous system, having the same composition, physical and chemical propertiesseparated from other parts of the system surface when switching through which the properties of the system are changing the jump. Phases are solid, liquid and gaseous. The homogeneous system always consists of one phase, heterogeneous - from several. According to the number of phases, the system is classified on single-phase, two-phase, three-phase, etc.
5. The first start of thermodynamics. Internal energy. Isobaric and isochhore thermal effects .
The first top of thermodynamics - One of the three major laws of thermodynamics is the law of conservation of energy for thermodynamic systems.
The first top of the thermodynamics was formulated in the middle of the XIX century as a result of the works of the German scientist Yu. R. Mayer, English physics J. P. Joule and German physics of Gelmholts.
According to the first beginning of thermodynamics, thermodynamic system can do work only at the expense of its internal energy or any external sources of energy .
The first top of the thermodynamics is often formulated as the impossibility of the existence of the perpetual engine of the first kind, which would perform work, without drawing energy from a source. The process flowing at a constant temperature is called isothermal, at constant pressure - isobaric, at a constant volume - isohoric. If during the process the system is isolated from the external environment in such a way that heat exchange with the medium is excluded, the process is called adiabatic.
Internal energy system.When switching the system from one state to another, some of its properties change, in particular internal energy. U.
The internal energy of the system is its total energy, which consists of the kinetic and potential energies of molecules, atoms, atomic nuclei and electrons. Internal energy includes the energy of translational, rotational and oscillatory movements, as well as the potential energy due to the forces of attraction and repulsion acting between molecules, atoms and intra-mattar particles. It does not include the potential energy of the position of the system in the space and the kinetic energy of the system movement as a whole.
Internal energy is the thermodynamic function of the system status. This means that whenever the system turns out to be in this state, its internal energy takes a certain meaning of this state.
ΔU \u003d U 2 - U 1
where u 1 and u 2 - the internal energy of the system inthe finite and initial states are conspirable.
The first law of thermodynamics.If the system is exchanged with an external thermal energy of q and mechanical energy (work) A, and at the same time passes from state 1 in state 2, the amount of energy that is released or is absorbed by the heat forms of the heat or the work of the operation of the system in transition from one Status to another and recorded.
Modern bioorganic chemistry - an extensive area of \u200b\u200bknowledge, the foundation of many medical disciplines and primarily biochemistry, molecular biology, genomics, proteomics and
bioinformatics, immunology, pharmacology.
The program is based on a systematic approach to the construction of the entire course on a single theoretical
basis based on the ideas about the electronic and spatial structure of organic
compounds and mechanisms of their chemical transformations. The material is represented in the form of 5 sections, the most important of which: "Theoretical bases of the structure of organic compounds and factors defining their reactivity", "biologically important classes of organic compounds" and "biopolymers and their structural components. Lipids"
The program is aimed at relevant teaching bioorganic chemistry in a medical university, and therefore discipline named "Bioorganic chemistry in medicine". Profiling to teach bioorganic chemistry to consideration of the historical relationship of the development of medicine and chemistry, including organic, increased attention to the classes of biologically important organic compounds (heterofunctional compounds, heterocycles, carbohydrates, amino acids and proteins, nucleic acids, lipids) as well as biologically important reactions of these compound classes ). A separate section of the Program is devoted to considering the pharmacological properties of some classes of organic compounds and the chemical nature of some classes of medicines.
Given the important role of "oxidative stress diseases" in the structure of the incidence of a modern person in the program, special attention is given to the reactions of free radical oxidation, the detection of finite products of free radical oxidation of lipids in laboratory diagnostics, natural antioxidants and antioxidant drugs. The program provides for consideration environmental problems, namely, the nature of xenobiotics and the mechanisms of their toxic action on living organisms.
1. Objective and learning tasks.
1.1. The purpose of training is the subject of bioorganic chemistry in medicine: to form an understanding of the role of bioorganic chemistry as a foundation of modern biology, theoretical basis for explaining the biological effects of bioorganic compounds, mechanisms of action of drugs and creating new drugs. To lay knowledge of the relationship of the structure, chemical properties and biological activity of the most important classes of bioorganic compounds, teach the applied knowledge gained when studying subsequent disciplines and in professional activities.
1.2. Supports of training of bioorganic chemistry:
1. Formation of knowledge of the structure, properties and mechanisms of reactions of the most important classes of bioorganic compounds caused by their medical and biological significance.
2. Formation of ideas about the electronic and spatial structure of organic compounds as a basis for explaining their chemical properties and biological activity.
3. Formation of skills and practical skills:
classify bioorganic compounds on the structure of carbon skeleton and functional groups;
use the rules of the chemical nomenclature to indicate the names of metabolites, medicines, xenobiotics;
determine reaction centers in molecules;
to be able to conduct high-quality reactions having a clinical and laboratory value.
2. Place of discipline in the PCO structure:
Discipline "Bioorganic chemistry" is an integral part of the discipline "Chemistry", which refers to the mathematical, natural-scientific cycle of disciplines.
The main knowledge necessary for studying disciplines is formed in the cycle of mathematical, natural-scientific disciplines: physics, mathematics; Medical informatics; chemistry; biology; Anatomy, histology, embryology, cytology; Normal physiology; Microbiology, virology.
It is preceding for studying disciplines:
biochemistry;
pharmacology;
microbiology, virology;
immunology;
professional disciplines.
Parallel disciplines, providing interdisciplinary bonds within the framework of the base part curriculum:
chemistry, physics, biology, 3. List of disciplines and the assimilation of which students are necessary for studying bioorganic chemistry.
General chemistry. The structure of the atom, the nature of chemical bond, types of ties, chemical classes, types of reactions, catalysis, medium reaction aqueous solutions.
Organic chemistry. Classes of organic substances, nomenclature of organic compounds, configuration of carbon atom, polarization of atomic orbitals, sigma and pi- communication. Genetic communication classes of organic compounds. The reactivity of different classes of organic compounds.
Physics. The structure of the atom. Optics - ultraviolet, visible and infrared spectrum areas.
The interaction of light with a substance is transmitting, absorption, reflection, scattering. Polarized light.
Biology. Genetic code. Chemical bases of heredity and variability.
Latin language. Mastering terminology.
Foreign language. The ability to work with foreign literature.
4. Sections of discipline and interdisciplinary connections with provided (subsequent)disciplines No. sections of this discipline necessary for studying the provisions provided No. The name provided by P / P (subsequent) disciplines (subsequent) disciplines 1 2 3 4 5 1 Chemistry + + + + + biology + - - + + biochemistry + + + + + + 4 Microbiology, virology + + - + + + 5 Immunology + - - - + Pharmacology + + - + + + 7 hygiene + - + + + professional disciplines + - - + + + 5. Requirements for the level of learning the content of the discipline Disciplines "Bioorganic Chemistry" provides for a number of targeted problem problems, as a result of which students need to be formed certain components, knowledge, skills, certain practical skills should appear.
5.1. The student must possess:
5.1.1. Communication competences:
the ability and willingness to analyze socially significant problems and processes, to use the methods of humanitarian, natural science, biomedical and clinical sciences in various types of professional and social activities in practice (OK-1);
5.1.2. Professional competencies (PC):
ability and readiness to apply the main methods, methods and means of obtaining, storing, processing scientific and professional information; receive information from various sources, including using modern computer tools, network technologies, databases and ability and willingness to work with scientific literature, analyze information, lead a search, turning read to a means to solve professional tasks (allocate the main provisions, effect from them and suggestions);
ability and readiness to participate in the formulation of scientific tasks and their experimental implementation (PC-2, PC-3, PK-5, PC-7).
5.2. The student should know:
Principles of classification, nomenclature and isomerism of organic compounds.
The fundamental basics of theoretical organic chemistry, which are the basis for studying the structure and reactivity of organic compounds.
The spatial and electronic structure of organic molecules and chemical transformations of substances that are participants in the processes of life, in direct communication with their biological structure, the chemical properties and the biological role of the basic classes of biologically important organic compounds.
5.3. The student must be able to:
Classify organic compounds on the structure of the carbon skeleton and by nature of functional groups.
To form formulas by names and called typical representatives of biologically important substances and drugs according to the structural formula.
Select functional groups, acidic and basic centers, conjugate and aromatic fragments in molecules to determine the chemical behavior of organic compounds.
Predict the direction and result of the chemical transformations of organic compounds.
5.4. The student must possess:
Skills of independent work with educational, scientific and reference literature; Search and make generalizing conclusions.
Have chemical dishes handling skills.
Have the skills of safe work in a chemical laboratory and the ability to handle caustic, poisonous, volatile organic compounds, working with burners, alcohol and electric heating devices.
5.5. Knowledge Control Forms 5.5.1. Current control:
Diagnostic control of mastering material. It is carried out periodically mainly to control the knowledge of the formula.
Training computer control at every occupation.
Test tasks requiring skills to analyze and summarize (see Appendix).
Planned colloquiums upon completion of the study of large sections of the program (see Appendix).
5.5.2 Total control:
Offset (held in two stages):
C.2 - Mathematical, natural science and medical and biological Total labor intensity:
2 Classification, Nomenclature and Classification and Classification Signs of Organic Modern Physico Compounds: The structure of the carbon skeleton and the nature of the functional group.
chemical methods Functional groups, organic radicals. Biology important research Bioorganic classes of organic compounds: alcohols, phenols, thiols, ethers, sulphides, aldehyde compounds, ketones, carboxylic acids and their derivatives, sulfonic acids.
the nomenclature of the Jew. Varieties of international nomenclature replacement and radical-functional nomenclature. Meaning of knowledge 3 Theoretical bases of the structure of organic compounds and the theory of structure of organic compounds AM Butlerova. The main factors determining their provisions. Structural formulas. The nature of the carbon atom on the position in the reaction capacity. chains. Isomeria as a specific phenomenon of organic chemistry. Types of stereoisomeria.
The chirality of organic compound molecules as a cause of optical isomerism. Stereoisomeria of molecules with one center of chirality (enantiomerium). Optical activity. Glycerin aldehyde as a configuration standard. Projection formulas Fisher. D and L-system of stereochemical nomenclature. Representations of R, s-nomenclature.
Stereoisomeria molecules with two or more centers of chirality: enantiomeria and diastereomeria.
Stereoisomeria in a series of double-connected compounds (pidiasteromeria). Cis- and trans-isomers. Stereoisomeria and biological activity of organic compounds.
The mutual influence of atoms: the causes of the occurrence, types and methods of its transfer in organic compounds molecules.
Conjugation. Coupling in open circuits (PI). Conjugated connections. Dien structures in biologically important compounds: 1,3-diene (butadiene), polyenes, alpha, beta-sunsited carbonyl compounds, carboxyl group. Conjugation as a system stabilization factor. Energy of pairing. Coupling in the arenas (PI) and in heterocycles (P-PI).
Aromaticity. Aromatic criteria. The flavoring of benzoid (benzene, naphthalene, anthracene, phenantrene) and heterocyclic (furan, thiophene, pyrrol, imidazole, pyridine, pyrimidine, purine) compounds. Wide prevalence of conjugate structures in biologically important molecules (Porphin, Gem, etc.).
Polarization of bonds and electronic effects (inductive and mesomeric) as a reason for the uneven distribution of electron density in the molecule. Substituents - electroneons and electron acceptors.
The most important substituents and their electronic effects. Electronic effects of substituents and the reactivity of molecules. Rule of orientation in the benzene ring, substituents I and II of the genus.
Acidness and basicity of organic compounds.
Acidness and basicity of neutral organic compound molecules with hydrogen-containing functional groups (amines, alcohols, thiols, phenols, carboxylic acids). Acids and bases according to Brenssululouuri and Lewis. Conjugated pairs of acids and bases. Acidity and stability of anion. Quantitative assessment of the acidity of organic compounds in terms of ka and rock values.
Acidity of various classes of organic compounds. Factors that determine the acidity of organic compounds: electronegability of the nonmetal atom (C-H, N - H, and O - H acid); polarizability of the nonmetal atom (alcohols and thiols, thiol poisons); The nature of the radical (alcohols, phenols, carboxylic acids).
The basicity of organic compounds. N-bases (heterocycles) and Pyension (alkenes, alkandeines, arena). Factors that determine the basicity of organic compounds: electronegate heteroatom (o- and notice); polarizability of the non-metal atom (o- and s-base); The nature of the radical (aliphatic and aromatic amines).
The value of the acid-base properties of neutral organic molecules for their reactivity and biological activity.
Hydrogen bond as a specific manifestation of acid-base properties. The general patterns of the reactivity of organic compounds as the chemical basis of their biological functioning.
Mechanisms of reactions of organic compounds.
Classification of the reactions of organic compounds according to the result Replacement, attachment, elimination, rearrangement, oxidizing agent and mechanism - radical, ionic (electrophyl, nucleophilic). Types of covalent bonding in organic compounds and particles formed: Gomolitic gap (free radicals) and heterolytic gap (carboations and carboanions).
The electronic and spatial structure of these particles and the factors resulting in their relative stability.
Homolytic reactions of radical substitution in alkanes with the participation of SP bonds of a 3-hybridized carbon atom. Reactions of free radical oxidation in a living cell. Active (radical) forms of oxygen. Antioxidants. Biological significance.
Electrophyl addition reactions (AE): heterolithic reactions involving a PI-communication. Mechanism of halogenation and ethylene hydration reactions. Acid catalysis. The influence of static and dynamic factors on the region selectivity of reactions. Features of the reactions of the addition of hydrogen-containing substances to pi-bonds in asymmetric alkenes. Markovnikov rule. Features of electrophile joining to conjugate systems.
Electful substitution reactions (SE): heterolithic reactions involving an aromatic system. The mechanism of reactions of electrophile substitution in the arenas. Sigma complexes. The reactions of alkylation, acylation, dense, sulfonia, halogenation of arena. Rule of orientation.
Deputy I-go and II. Features of electrophilic reactions in heterocycles. The orienting effect of heteroatoms.
The reactions of nucleophilic substitution (SN) at a SP3-hybridized carbon atom: heterolithic reactions caused by the polarization of the sigma bondage of carbon-heteroatom (halogen derivatives, alcohols). Effect of electronic and spatial factors on the reaction capacity of compounds in nucleophilic substitution reactions.
Hydrolysis reaction halogen derivatives. Alkylation reactions of alcohols, phenols, thiols, sulphides, ammonia and amines. The role of acid catalysis in the nucleophilic substitution of the hydroxyl group.
Disamination of compounds with primary amino group. The biological role of alkylation reactions.
Elimination reactions (dehydrogalogenation, dehydration).
Elevated CH-acidity as the cause of elimination reactions accompanying nucleophilic substitution in a SP3-hybridized carbon atom.
The reactions of nucleophilic addition (AN): heterolithic reactions with the participation of carbon-oxygen pi-bond (aldehyde, ketones). Classes of carbonyl compounds. Representatives. Obtaining aldehydes, ketones, carboxylic acids. The structure and reactivity of the carbonyl group. The influence of electronic and spatial factors. The mechanism of reactions AN: the role of protonation in increasing the reaction capacity of carbonyl. Biologically important reactions of aldehyd and ketones Hydrogenation, oxidation-reduction of aldehydes (dismantia reaction), oxidation of aldehydes, the formation of cyanhydrines, hydration, the formation of semi-acetals, imine. Aldol deal reactions. Biological significance.
The reactions of nucleophilic substitution in the SP2 hybridized carbon atom (carboxylic acids and their functional derivatives).
The mechanism of nucleophilic substitution reactions (Sn) in SP2Hybridized carbon atom. The acylation reactions - the formation of anhydrides, esters, complex thioethers, amides, and inverse the reactions of hydrolysis. The biological role of acylation reactions. Acid properties of carboxylic acids on the ON group.
Reactions of oxidation and restoration of organic compounds.
Redox reactions, electronic mechanism.
The degree of oxidation of carbon atoms in organic compounds. Oxidation of primary, secondary and tertiary carbon atoms. Oxidation of various classes of organic compounds. Ways to utilize oxygen in a cell.
Energy oxidation. Oxidase reactions. The oxidation of organic substances is the main source of energy for chemotrofs. Plastic oxidation.
4 Biologically important classes of organic compounds Multiatomic alcohols: ethylene glycol, glycerin, inosit. Hydroxy acid formation: classification, nomenclature, representatives of dairy, betaonessyllane, gammaoxymal, apple, wine, lemon, restorative amination, reaminting and decarboxylation.
Amino acids: classification, representatives of beta and gammaisomers aminopropane, gammaamic oil, epsilonamicapron. Salicylic acid reaction and its derivatives (acetylsalicylic acid antipyretic, anti-inflammatory and antipers, enteroseptol and 5-nct. The isoquinoline core as the basis of alkaloids of spasmolytic (papaverine) and analgesics (morphine). Derivatives of acridine disinfectants.
ksanthina derivatives - caffeine, theobromin and theophiline, indole derivatives reserpine, Strichnin, Pilocarpine, chinoline derivatives - chinin, isoquinoline morphine and papaverine.
cefalosproines are trefalospioran derivatives, tetracycles naphtacene derivatives, streptomycins - amyloglycosides. Semi-synthetic 5 biopolymers and their structural components. Lipids. Definition. Classification. Functions.
Cyclo-oxotomeria. Mutarization. Deroxachara monosaccharide derivatives (deoxyribosis) and amino-amahar (glucosamine, galactosamine).
Oligosaccharides. Disaccharides: maltose, lactose, sucrose. Structure. Firecosium connection. Restoring properties. Hydrolysis. Biological (the path of decomposition of amino acids); Radical reactions - hydroxylation (formation of amino acid hydroxy derivatives). The formation of peptide communications.
Peptides. Definition. The structure of the peptide group. Functions.
Biologically active peptides: glutathione, oxytocin, vasopressin, glucagon, neuropeptides, kinin peptides, immunoactive peptides (thymbosin), inflammation peptides (dipxen). Concept of cytokines. Antibiotic peptides (gramicidine, actinomycin D, cyclosporin A). Peptides-toxins. The relationship of biological effects of peptides with certain amino acid residues.
Proteins. Definition. Functions. Levels of protein structure. The primary structure is the sequence of amino acids. Research methods. Partial and complete protein hydrolysis. The value of determining the primary structure of proteins.
Directional place-specific mutagenesis as a method for studying the relationship of the functional activity of proteins with primary structure. Congenital disorders of the primary structure of proteins - point mutations. Secondary structure and its types (alpha spiral, beta structure). Tertiary structure.
Denature. The concept of active centers. Quaternary structure of oligomeric proteins. Cooperative properties. Simple and complex glycoprotein proteins, lipoproteins, nucleoproteins, phosphoproproids, metalloproteides, chromoproteins.
Nitrogen bases, nucleosides, nucleotides and nucleic acids.
Determination of the concepts of a nitrogen base, nucleoside, nucleotide and nucleic acid. Purine (adenine and guanine) and pyrimidine (uracil, thymine, cytosine) nitrogenous bases. Aromatic properties. Resistance to oxidative decay as a basis for the fulfillment of the biological role.
Laktim is a lactam tautomeria. Minor nitrogen bases (hypoxanthine, 3-N-methyluracyl, etc.). Derivatives of nitrogen bases - antimetabolites (5-fluorouracil, 6-mercaptopurine).
Nucleosides. Definition. The formation of a glycoside relationship between a nitrogen base and pentose. Hydrolysis of nucleosides. Nucleosydimatimetabolites (adenine arabinoside).
Nucleotides. Definition. Structure. The formation of phosphoeter communication with esterification of C5 hydroxyl pentose phosphoric acid. Hydrolysis of nucleotides. Nucleotides-macroeergi (nucleosidepolyphosphates - ADP, ATP, etc.). Nucleotides-coefficers (above +, phad), structure, role of vitamins B5 and B2.
Nucleic acids - RNA and DNA. Definition. Nucleotide composition of RNA and DNA. Primary structure. Phosphodieter communication. Hydrolysis of nucleic acids. Defining the concepts of triplet (codon), gene (cystroon), genetic code (genome). International project "Man's Genome".
Secondary DNA structure. The role of hydrogen bonds in the formation of the secondary structure. Complete pairs of nitrogen bases. Tertiary DNA structure. Changes in the structure of nucleic acids under the influence of chemicals. The concept of substances mutagen.
Lipids. Definition, classification. Washed and unlimited lipids.
Natural higher fatty acids - lipid components. The most important representatives: palmitic, stearinovaya, oleic, linolevial, linolenic, arachidon, eikosopentaena, approxocent (vitamin F).
Neutral lipids. Acilglycerin - Natural Fats, Oils, Wax.
Artificial food hydrins. The biological role of acylglycerin.
Phospholipids. Phosphatidic acids. Phosphatidylcholines, phosphatidatehanolamines and phosphatidylserine. Structure. Participation in the formation of biological membranes. Lipid peroxidation in cell membranes.
Sphingolipid. Sphinosin and Sphingomyelina. Glycolipids (cerebroids, sulfatis and gangliosides).
Unlimited lipids. Terpene. Mono- and bicyclic terpinas 6 Pharmacological properties The pharmacological properties of some classes of mono-poly and some classes of heterofunctional compounds (halogenerates, alcohols, hydroxy- and organic compounds. Oxocuslots, benzene derivatives, heterorocycles, alkaloids.). Chemical chemical nature of some nature of anti-inflammatory, analgesics, antiseptics and drug classes. Antibiotics.
6.3. Sections of disciplines and types of classes 1. Introduction to the subject. Classification, nomenclature and studies of bioorganic compounds 2. Theoretical foundations of the structure of organic reactivity.
3. Biologically important classes of organic 5 pharmacological properties of some classes of organic compounds. The chemical nature of some classes of drugs of the L ( PZ - practical classes; LR - laboratory work; C - seminars; SRS - independent work of students;
6.4 Thematic plan of lectures on discipline 1 1 Introduction to the subject. The history of the development of bioorganic chemistry, the value for 3 2 the theory of the structure of organic compounds A.M. Butlerova. Isomerius as 4 2 Mutual influence of atoms: causes of occurrence, types and methods of its transmission in 7 1.2 test work on the sections "Classification, nomenclature and modern physicochemical methods of study of bioorganic compounds" and "Theoretical foundations of the structure of organic compounds and factors defining their reaction 15 5 Pharmacological properties of some classes of organic compounds. Chemical 19 4 14 Detection of insoluble calcium salts of higher carboxylices 1 1 Introduction to the subject. Classification and work with recommended literature.
nomenclature of bioorganic compounds. Performing a written task for 3 2 Mutual influence of atoms in molecules Working with recommended literature.
4 2 Acidness and basicity of organic work with recommended literature.
5 2 Mechanisms of organic reactions work with recommended literature.
6 2 Oxidation and restoration of organic work with recommended literature.
7 1.2 Examination on sections Work with recommended literature. * Modern physico-chemical methods offered topics, conducting a study of bioorganic compounds "of information retrieval in various organic compounds and factors, internet and work with English-speaking bases 8 3 heterofunctional bioorganic work with recommended literature.
9 3 biologically important heterocycles. Work with recommended literature.
10 3 Vitamins (laboratory work). Work with recommended literature.
12 4 alpha amino acids, peptides and proteins. Work with recommended literature.
13 4 Nitrogen bases, nucleosides, work with recommended literature.
nucleotides and nucleic acids. Performing a written task on writing 15 5 Pharmacological properties of some work with recommended literature.
classes of organic compounds. Performing a written task on writing the chemical nature of some classes chemical formulas Some medicinal * - tasks for the selection of a student.
organic compounds.
organic molecules.
organic molecules.
organic compounds.
organic compounds.
connections. Stereoisomeria.
some classes of medicines.
For the semester, the student can dial the maximum 65 points on practical activities.
At one practical lesson, the student can maximize 4.3 points. This number is made up of points gained for visiting classes (0.6 points), the task of extracurricular independent work (1.0 points), laboratory work (0.4 points) and points accrued for the oral response and test task (from 1.3 to 2.3 points). Points for visiting the classes, the fulfillment of the task of extracurricular independent work and laboratory work is charged according to the principle "Yes" - "No". Points for the oral response and test task are accrued differentiated from 1.3 to 2.3 points in cases of positive responses: 0-1.29 points corresponds to the evaluation "unsatisfactory", 1.3-1.59 - "satisfactory", 1.6 -1.99 - "Good", 2.0-2.3 - "excellent." In the test work, the student can maximize 5.0 points: a visit to the occupation of 0.6 points and the oral response of 2.0-4.4 points.
For admission to test, the student must score at least 45 points, while the current student performance is assessed as follows: 65-75 points - "excellent", 54-64 points - "Good", 45-53 points - "satisfactory", less than 45 Points are unsatisfactory. If the student is gaining from 65 to 75 points ("excellent" result), then it is freed from the credit and receives the "Offset" mark in the test book automatically, gaining up for offset 25 points.
At the standings, the student can dial 25 points as possible: 0-15.9 points corresponds to the evaluation "unsatisfactory", 16-17.5 - "satisfactory", 17.6-21.2 - "Good", 21.3-25 - " excellent".
Distribution of premium points (only up to 10 points per semester) 1. Visit to the lecture - 0.4 points (100% visiting lectures - 6.4 points per semester);
2. Participation in UIRS to 3 points, including:
writing an essay on the topic offered - 0.3 points;
preparation of the report and multimedia presentation for the final educational and theoretical conference 3. Participation in Nirs - up to 5 points, including:
visit the meeting of the student scientific circle at the Department - 0.3 points;
preparation of the report to the meeting of the student scientific circle - 0.5 points;
speech with a report at the university student scientific conference - 1 point;
speech with a report at the regional, All-Russian and International Student Scientific Conference - 3 points;
publication in collections of student scientific conferences - 2 points;
publication in a peer-reviewed scientific journal - 5 points;
4. Participation in educational work at the Department of Up to 3 points, including:
participation in the organization of the activities held by the Department of Events for Educational Work in the extracurricular time - 2 points for one event;
a visit to the activities held by the Department of Events for Educational Work in the extracurricular time - 1 point for one event;
The distribution of penalty points (only up to 10 points per semester) 1. The absence on the lecture on a disrespectful reason, 0.66-0.67 points (0% of visits to lectures - 10 points for if the student missed an exercise for a good reason, he has the right to work out To enhance your current rating.
If the missing is disrespectful - the student must work out the occupation and obtain an estimate with a downstream coefficient of 0.8.
If the student is freed from the physical presence in class (by order of the Academy), then he is charged maximum pointsIf a task is made on extracurricular independent work.
6. Educational and methodical and informational support of discipline 1. N.A.Tyukavkina, Yu.I. Baukov, S.E. Zuraban. Bioorganic chemistry. M.: Drop, 2009.
2. Tubavkina N.A., Baukov Yu.I. Bioorganic chemistry. M.: Drop, 2005.
1. Ovchiknikov Yu.A. Bioorganic chemistry. M.: Enlightenment, 1987.
2. Rails A., Smith K., Ward R. Basics of organic chemistry. M.: Mir, 1983.
3. Shcherbak I.G. Biological chemistry. Tutorial for medical universities. S.-P. Publishing house SPBGMU, 2005.
4. Berezov T.T., Korovkin B.F. Biological chemistry. M.: Medicine, 2004.
5. Berezov T.T., Korovkin B.F. Biological chemistry. M.: Medicine, Additions V.V., Ryabtseva E.G. Biochemical organization of cell membranes ( tutorial For students of pharmaceutical faculties of medical universities). Khabarovsk, DVGMU. 2001
7. SOROSE EDUCATIONAL JOURNAL, 1996-2001.
8. Guide to K. laboratory activities on bioorganic chemistry. Edited by N.A. Dukkavina, M.:
Medicine, 7.3 Educational materials prepared by the Department 1. Methodical development of practical training in bioorganic chemistry for students.
2. Methodological developments of independent extracurricular work of students.
3. Borodin E.A., Borodina G.P. Biochemical diagnosis (physiological role and diagnostic value of biochemical indicators of blood and urine). Tutorial Edition 4. Blagoveshchensk, 2010.
4. Borodina G.P., Borodin E.A. Biochemical diagnosis (physiological role and diagnostic value of biochemical indicators of blood and urine). Electronic study guide. Blagoveshchensk, 2007.
5. Tasks for computer testing of knowledge of students on bioorganic chemistry (Cost. Borodin E.A., Doroshenko G.K., Egorshina E.V.) Blagoveshchensk, 2003.
6. Test tasks for bioorganic chemistry to the exam on bioorganic chemistry for students of the medical faculty of medical universities. Toolkit. (Sost. Borodin E.A., Doroshenko G.K.). Blagoveshchensk, 2002.
7. Test tasks for bioorganic chemistry to practical exercises on bioorganic chemistry for students of the medical faculty. Toolkit. (Sost. Borodin E.A., Doroshenko G.K.). Blagoveshchensk, 2002.
8. Vitamins. Toolkit. (Sost. Erhorshina E.V.). Blagoveshchensk, 2001.
8.5 Ensuring discipline Equipment and educational materials 1 Chemical dishes:
Glassware:
1.1 Test tubes Chemical 5000 Chemical experiments and analyzes in practical classes, UIRS, 1.2 Test tubes Centrifuge 2000 Chemical experiments and analyzes in practical classes, UIRS, 1.3 Glass sticks 100 Chemical experiments and analyzes in practical training, UIRS, 1.4. Flasks of various volumes (for 200 chemical experiments and analyzes in practical classes, UIRS, 1.5 Bolshoi flasks - 0.5-2.0 30 Chemical experiments and analyzes in practical training, UIRS, 1.6 Chemical glasses of various 120 chemical experiments and analyzes on practical Classes, UIRS, 1.7 Chemical glasses of large 50 chemical experiments and analyzes in practical classes, UIRS, cooking workers 1.8 Flasks of various volumes of 2000 Chemical experiments and analyzes in practical training, UIRS, 1.9 Filtering funnels 200 Chemical experiments and analyzes in practical training, WERS , 1.10 Glassware Chemical experiments and analyzes in practical training, UIRS, chromatography, etc.).
1.11 Alcohol 30 Chemical experiments and analyzes in practical classes, UIRS, Porcelainware 1.12 Glassesmiscellaneous volume (0.2-30 Preparation of reagents on practical classes 1.13 Mortar with pestles Preparation of reagents for practical classes, chemical experiments and 1.15 cups for evaporation 20 Chemical experiments and analyzes in practical training, UIRS, measuring dishes:
1.16 Measuring flasks of various 100 Preparation of reagents for practical classes, chemical experiments 1.17 Measuring cylinders of various 40 preparation of reagents for practical classes, chemical experiments 1.18 Menzurics of various volumes 30 Preparation of reagents for practical classes, Chemical experiments 1.19 Pipettes measuring on 2000 Chemical experiments and analyzes in practical Classes, UIRS, micropipettes) 1.20 Mechanical automatic 15 Chemical experiments and analyzes in practical classes, UIRS, 1.21 Mechanical automatic 2 Chemical experiments and analyzes in practical training, UIRS, VARIATIVES 1.22 Dispensers 1.22 Electronic automatic 1 Chemical experiments and analyzes in practical exercises, UIRS, 1.23 Microfits of AC 5 Chemical experiments and analyzes in practical training, UIRS, 2 Technical equipment:
2.1 Tripods for test tubes 100 Chemical experiments and analyzes in practical training, UIRS, 2.2 Triples for pipettes 15 Chemical experiments and analyzes in practical training, UIRS, 2.3 Students Metal 15 Chemical experiments and analyzes in practical classes, WERS, Heating appliances:
2.4 Drying Cabinets 3 Drying Chemical Cookware from Glass, Conducting Chemical 2.5 Thermostats Air 2Thermostatting of the incubation mixture in determining 2.6 Thermostats Water 2 Thermostatting of the incubation mixture in determining 2.7 Power plants 3 Preparation of reagents on practical classes, chemical experiments and 2.8 refrigerators with freezing 5 Storage of chemicals, solutions and biological material for Chinar cameras, Biryusi, practical training , UIRS, NERS "Stinol"
2.9 storage cabinets 8 storage of chemicals chemicals 2.10 Metal safe 1 storage of poisonousreagents and ethanol 3 general purpose equipment:
3.1 Analytical damper 2 gravimetric analysis in practical classes, UIRS, NERS 3.6 Ultracentrifugu 1 Demonstration of the method of sedimentation analysis on practical (Germany) 3.8 Magnetic stirrers 2 Preparation of reagents for practical classes 3.9 DEFLINER DEVERATIVE DEE-1 OPERATION OF DISTENED WATER CREATE WATER 3.10 THERMOMETERS 10 Temperature control when conducting chemical analyzes at 3.11 Set of ranges 1 Measurement of density of solutions 4 Special purpose equipment:
4.1 Electrophoresis apparatus 1 Demonstration of the electrophoresis method of serum proteins by 4.2 Electrophoresis apparatus in 1 Demonstration of the separation of serum lipoproteins 4.3 Equipment for a column Demonstration of protein separation method using chromatography 4.4 Equipment for the demonstration of the TLC method for dividing lipids on practical chromatography in thin layer. Classes, NURS Measuring equipment:
Photoelectrocolorimeters:
4.8 Photometer "Solar" 1 Measurement of light absorption of painted solutions at 4.9 Spectrophotometer SF 16 1 Measurementlight absorption of solutions in visible and UV regions 4.10 Clinical spectrophotometer 1 Measurement of light absorption solutions in visible and UV areas "Schimadzu - CL-770" spectrum when using spectral definition methods 4.11 High-efficient 1 Demonstration of HPLC method (practical classes, UIRS, NERS) Liquid chromatograph "Milichrom - 4".
4.12 Polarimeter 1 Demonstration of optical activity of enantiomers, 4.13 Refractometer 1 Demonstrationrefractometric method of definition 4.14 pH meters 3 Preparation of buffer solutions, Demonstration of buffer 5 Projection equipment:
5.1 Multimedia Projector and 2 Demonstration of Multimedia Presentations, Photo- and Diaprints: Demonstrationslides at lectures and practical classes 5.3 "Pereleng-semi-automatic" 5.6 The device for the demonstration is fixed behind the morphological training case. Demonstration of transparent films (Overhead) and illustrative material at lectures, during UIRS and NERS film projector.
6 Computing Technology:
6.1 Cathedral of 1 access to Internet educational resources (national and personal computers with international electronic databases in chemistry, biology and Internet access medicine) for teachers of the Department and Students in Educational and 6.2 Personal Computers 8 Creating Teachers of the Department of Printed and Email Ceads Didactic materials during educational and methodical work, 6.3 Computer class at 10 1 Programmed testing of students' knowledge on the landing places of practical training, during tests and exams (current, 7 Tutorials:
1. Peptide communications.
2. Regularity of the structure of the polypeptide chain.
3. Types of ties in the protein molecule.
4. Disulfide bond.
5. Specific specificity of proteins.
6. Secondary structure of proteins.
7. The tertiary structure of proteins.
8. Mioglobin and hemoglobin.
9. Hemoglobin and its derivatives.
10. Blood plasma lipoproteins.
11. Types of hyperlipidemias.
12. Electrophoresis of proteins on paper.
13. Scheme of protein biosynthesis.
14. Collagen and tropocoleggen.
15. Mozin and Aktin.
16. Avitamin RP (Pellagra).
17. Avitaminosis B1.
18. Avitamin S.
19. Avitaminosis A.
20. Avitaminosis D (Rakhit).
21. Prostaglandins are physiologically active derivatives of unsaturated fatty acids.
22. Nerokoxins formed from catechamins and indolamines.
23. Products are not enzymatic reactions of dopamine.
24. Neuropeptides.
25. Polyunsaturated fatty acids.
26. The interaction of liposomes with a cell membrane.
27. Free oxidation (distinction with tissue breathing).
28. PNCC of Omega 6 and Omega 3 families.
2 Sets of slides on various sections of the program 8.6 Interactive learning tools (Internet technologies), multimedia materials, electronic libraries and textbook, photo and video materials 1 Interactive learning tools (Internet technologies) 2 Multimedia materials Stonik V.A. (Tiboch DNC SB RAS) "Natural compounds - the basis of 5 Borodin E.A. (AGMA) "The human genome. Genomics, proteomics and author's presentation 6 Pivovarova E.N. (IZGC SO RAMS) "The role of regulation of gene expression author's presentation of a person."
3 Electronic libraries and textbooks:
2 MEDLINE. CD version of electronic databases for chemistry, biology and medicine.
3 Life Sciencies. CD version of electronic databases for chemistry and biology.
4 Cambridge Scientific Abstracts. CD version of electronic databases for chemistry and biology.
5 PubMed - electronic database of the National Institute of Health http://www.ncbi.nlm.nih.gov/pubmed/ Organic Chemistry. Digital library. (Sost. N.F. Tubavkin, A.I. Tailova) - M., 2005
Organic and general chemistry. Medicine. Lectures for students, course. (Electronic manual). M., 2005
4 Videos:
3 MES Tiboch DNC DVO RAS CD
5 photos - video footage:Copyright photo and video footage. cafe. prof. E.A. Borodina about 1 universities UPSAL (Sweden), Granada (Spain), medical schools of Japan Universities (GGNIGAT, Osaka, Canadzava, Hiroshaki), IBMX RAMS, IFCHM MS of Russia, Tibooche DNC. DVO RAS.
8.1. Examples of test tasks of current control (with reference standards) to occupation №4 "Acidity and basenessorganic Molecules "
1. Select the characteristic signs of Brensted-Lowry acids:
1. The concentration in aqueous solutions of hydrogen ions 2. The concentration of hydroxide ion concentrations in aqueous solutions 3. The proton donors are 4. The protons with neutral molecules and ions - proton acceptors 5. The factors are influenced by affecting the acidity of organic molecules:
1. Electricity of heteroatoma 2. Heteroatomy 3. Radical heteroatomy. Justice to dissociation 5. Water solubility 3.Select the strongest acids of Brensteads from the listed compounds:
1. The 2.amines 3. Snirts 4.Tiols. 5.Qarboxylic acids 4. Decide the characteristic features of organic compounds with base properties:
1. Proton acceptors 2. DONORS OF PROTONS 3. DISSOCIATION DISSOCIATION DOWN HYDROXY ions 4. Divociated 5. The main properties determine the reaction capacity 5. Select the weakest base from the above connections:
1.Mamiak 2.Metylamine 3.Phenylamine 4.Thylamine 5.Propylamine 8.2 Examples of current control situational problems (withequalons of responses) 1. Determine the general structure in conjunction:
Decision. The choice of the source structure in the structural formula of the organic compound is regulated in the reactive nomenclature of the Jewberry number of consistently applied rules (see Tutorial, 1.2.1).
Each subsequent rule applies only when the previous one does not allow you to make an unambiguous choice. Compound I contains aliphatic and alicyclic fragments. According to the first rule, the elemental characteristic group is selected as a general basis. Of the two components of the characteristic groups (it and NH,) the senior is the hydroxyl group. Therefore, the investigative will be the structure of cyclohexane, which is reflected in the title of this compound - 4-aminomethylcyclohexanol.
2. The basis of a number of biologically important compounds and drugs is a condensed heterocyclic purine system, including pyrimidine and imidazole kernels. What is explained by the increased resistance of Pyrin to oxidation?
Decision. Aromatic compounds have a large pairing energy and thermodynamic stability. One of the manifestations of aromatic properties is resistance to oxidation, although "extern"
aromatic compounds have high degree Unsaturation, which usually determines the tendency to oxidation. To respond to the task assigned to the condition, it is necessary to establish the pyrine affiliation to aromatic systems.
According to the determination of aromaticity, the necessary (but insufficient) condition for the occurrence of a conjugate closed system is the presence of a flat cyclic-silver molecule with a single electronic cloud. In the Purin molecule, all carbon and nitrogen atoms are in a state of SP2 hybridization, and therefore all asvia are lying in the same plane. Due to this, the orbital of all atoms included in the cycle are located perpendicular to the plane -cakely and parallel to each other, which creates conditions for their mutual overlap to form a single closed delocaliso-bathroom of the T-electronic system covering all cycle atoms (circular pairing).
The aromaticity is also determined by the number -Electrons, which must correspond to the formula 4/7 + 2, where P is a number of natural numbers O, 1, 2, 3, etc. (Hyukkel rule). Each carbon atom and pyridine nitrogen atoms in positions 1, 3 and 7 are added to the conjugate system by one P-electron, and the pyrrol atom of nitrogen at position 9 is a watered pair of electrons. The maturium conjugate system contains 10-electrons, which corresponds to the Hyukkel rule at n \u003d 2.
Thus, the pyrine molecule has an aromatic character and its resistance to oxidation is associated with it.
The presence in the cycle of purine heteroatoms leads to unevenness in the distribution of the electronic density. Pyridine nitrogen atoms exhibit electronically accurate character and reduce electron density on carbon atoms. In this regard, the oxidation of Purin, considered in the general case as the loss of electrons by an oxidizing compound, will be even more difficult compared to benzene.
8.3 Test assignments to a test (one option in full with reference standards) 1. Name organogenic elements:
7.Si 8.fe 9.CU 2. Suggest functional groups having a PI communication:
1. CARBOXY 2. AMINOGRUP 3. Hydroxyl 4. Sign 5.Karboonile 3. Learn the older functional group:
1.-C \u003d O 2.-SO3N 3.-CII 4.-SOM 5.-Oh 4. What class of organic compounds relate to lactic acid CH3-Sony-coxy, formed in tissues as a result of anaerobic glucose decay?
1. Curboxylic acids 2. Osic acids 3. Assoculotes 4. Baseline 5. Note by replacement nomenclature The substance that is the main energy fuel cell and having the following structure:
CH2-CH -CH -SN -SN -S \u003d O
I III I
Oh Oh Oh Oh n
1. 2,3,4,5,6-pentagidroxygexanal 2.6-Oxohexanentanol 1,2,3,4, 3. Glucose 4.Gexose 5.1,2,3,4,5-pentagidroxygexanal- 6. Tell the characteristic features of conjugate systems:1. Evilization of electronic density of sigma- and pins 2. Support and low reactivity 3. Reityfulness and high reactivity 4. Conducting alternating sigma- and 5. -Pupplence pi-links are separated by -CH2 groups of 7. What compounds Characterist Pi-pi pairing:
1.Carotins and vitamin A 2.Pirrol 3.Pyridine 4.Porphyrine 5.Benzpires 8.Select the substituents of the type I focusing in ortho and pair positions:
1. Alkyls 2.- It is 3.- NH 4.- Soam 5.- SO3H 9. As the effect has a group in aliphatic alcohols:
1. Inductive inductive 2.-negative inductive 3. positive mesomeric 4. negative mesomeric 5.Type and the effect of the effect depend on the position of the group 10.Seate the radicals that have a negative mesomeric effect 1.Halogen 2. alkyl radicals 3. MineGroup 4.Hidroxigroup 5.Qarboxygroup 11.Select the characteristic features of Brenstened-Lowry acids:
1. The concentration in aqueous solutions of hydrogen ions 2. The concentration in aqueous solutions of hydroxide ions is performed 3. The names are neutral and ions - proton donors 4. The protons are neutral and ions - the proton acceptors 5. Therefore affect the reaction of the medium 12. For factors. affecting the acidity of organic molecules:
1.Electricatence of heteroatom 2. Heteroatoma 3. Radical drill. Justice to dissociation 5. Water solubility 13. Select the most strong acids of Brensteads from listed compounds:
1. Levels 2. Mine 3.Spirts 4.Tiols 5.Qarboxylic acids 14. Tell the characteristic features of organic compounds with the properties of the grounds:
1. Proton acceptors 2. DONOR protons 3. Dissociations give hydroxyl ions 4. Divociated 5. -Wound properties determine the reaction capacity 15. Select the weakest base from the above connections:
1.Mamiak 2.Metylamine 3.Phenylamine 4.Ethylamine 5.Propylamine 16. What signs are used to classify the reactions of organic compounds:
1. Mechanism of the chemical bonding 2.The results of the reaction 3. The number of molecules involved in the stage determining the speed of the entire process 4. The image of the attacking reagent connection 17.Select the active forms of oxygen:
1. Single oxygen 2. Peroxide biradical -o-osoupe oxide ion 4. Hydroxyl radical 5.Tractive molecular oxygen 18. Select the characteristic signs of electrophyl reagents:
1. Pacifics that carry partial or full positive charge 2. Causes with a homologous break of covalent coupling 3. Pachentians carrying an unpaired electron electron carrier, carrying partial or complete negative charge 5. Causes with a heterolithic covalent bond. 19.Select the compounds for which The reactions of electrophile substitution are characteristic:
1. Alkanes 2.Anes 3. Tools 4.Anomatic heterocycles 5. Levels 20. Here, the biological role of the reactions of free-radical oxidation:
1. Phaganoic activity of cells 2.Universal mechanism for the destruction of cell membranes 3. The presentation of cellular structures 4. Perform a decisive role in the development of many pathological processes 21. Select for which classes of organic compounds is characterized by nucleophilic replacement:
1. Snaps 2. The 4.Galogeneous hydrocarbons 4.Tioles 5.Lehydes 22. In which sequence reduces the reactivity of substrates in nucleophilic replacement reactions:
1. Halmetrogen derivatives of alcohol amines 2.amine alcohols Halogene derivatives of hydrocarbons 3. Amina halogen production hydrocarbons 4.Galogeneous hydrocarbons Amina alcohol 23.Select polymatomic alcohi from listed compounds:
1. ethanol 2.Thylen glycol 3. Glycerin 4.xilite 5.Sorbitates 24.Select characteristic of this reaction:
CH3-CH2ON --- CH2 \u003d CH2 + H2O 1. Reactivity of elimination 2. Reactivity of intramolecular dehydration 3.Reals in the presence mineralic acids When heated 4. Proteces under normal conditions 5. Reactivity of intermolecular dehydration 25. What properties appear with the introduction of chlorine in the organic substance molecule:
1. Narcotic properties 2. Lacking (tear) 3.Acteptic properties 26. Select reactions characteristic of SP2-hybridized carbon atom in oxo compounds:
1.Nochlorophilic addition 2.Nochelophilic substitution 3.Electrophilic connection 4.Gomolytic reactions 5. Motterolytic reactions 27. In which sequence, the ease of the nucleophilic attack of carbonyl compounds decreases:
1. Aldeehydical-chiderhydrideyeticiamidisols of carboxylic acids 2. Butonaldecarboxylic acids 3. Yungidcarboxylic acids 28. Directly characteristic of this reaction:
1. Complete reaction to aldehyde 2.aldehyde - reducing agent, silver oxide (I) - oxidizing agent 3.Aldehyde - oxidizing agent, silver oxide (I) - reducing agent 4. Oxidation-reducing reaction 5.Things in an alkaline medium 6. Cauctees for ketones 29 What from the above carbonyl compounds are subject to decarboxylation with the formation of biogenic amines?
1. CARBONICICICICS 2. SAMINISTURES 3. SOCIATURES 4. Oxyxylotes 5.Benzoic acid 30. How acidic properties are changed in the homologous row of carboxylic acids:
1. Increase 2. Dimensions 3. It is changed 31. Whats from the proposed compound classes refer to heterofunctional:
1. Oncexic acids 2. Sociality 3.Inhibries 4.Inoxylots 5.Dicarboxylic acids 32.k oxyc acids include:
1.Limonaya 2.Masyl and acetate 4.Pillinginograde 5.Yube 33.Select medicines - Salicylic acid derivatives:
1.Parazetomol 2.Fenacetin 3. Sulfanimamides 4.Aspirin 5.Pask 34.Select medicines - derivatives of p-aminophenol:
1.Parazetomol 2.Phenacetin 3. Sulfanimamides 4.Aspirin 5.Pask 35.Select medicines - sulfanyl acid derivatives:
1.Parazetomol 2.Fenacetin 3. Sulfanimamides 4.Aspirin 5.Pask 36.Select the main provisions of AM Butler's theory:
1. Carbonautomas are connected by simple and multiple bonds 2. Carbon in organic compounds of four-tape 3. Functional group determines the properties of the substance of the carbon. The carbon matters form open and closed cycles 5. In the organic compounds, carbon is in a reduced form.
1. Drug 2. The location of multiple bonds of 3.Functional groups 4. Design 5. Configuration 38.Select what is characteristic of the concept of "conformation":
1. The possibility of rotation around one or more sigma of bonds 2. Conforters is an isomer 3. By changing the sequence of links. 4. By changing the spatial location of the substituents 5. By changing the electronic structure 39.Seate the similarity between enantiomers and diastereomers:
1. Regarding the same physicochemical properties. 2. Delive to rotate the plane of the polarization of light 3. It is capable of rotating the plane of the polarization of light 4. The existence of a center of chirality 40. Select the similarities between the configuration and conformational isomeria:
1. Insometer is associated with different positions in the space of atoms and groups of atoms 2. The system is separated by the rotation of atoms or groups of atoms around the sigma coupling. 3. Resomery is due to the presence in the molecule of the center of chirality.
41. Name the heteroatoms included in biologically important heterocycles:
1.Azot 2. Forosphorus 3. Callery 5.Cyclood 42. Here, a 5-membered heterocycle, which is part of the porphyrins:
1.Pirrolidine 2. Iimidazole 3.Pirrol 4.Pizole 5.Furane 43.An a heterocycle with one heteroatom is part of nicotinic acid:
1.Purine 2.Piridin 3.Pyrrol 4.Pyridin 5.Pirimidine 44. Name the final poirin oxidation product in the body:
1.Gipoxanthine 2.xanthin 3.Moisy acid 45.Close opium alkaloids:
1.Stricine 2.Papalerin 4. Morphin 5. Racing 6.Hinin 6. What oxidation reactions are characteristic of the human body:
1. Dehydrification 2. Electron Oxygen Connection 3. Halogens 4. Digitalize Halogens 5. Recovery with potassium permanganate, nitric and chlorine acids 47. And the degree of oxidation of carbon atom in organic compounds is determined:
1. Its connections with atoms of elements, more electronegative than hydrogen 2. His links with oxygen atoms 3. Its connections with hydrogen atoms 48. What compounds are formed when the primary carbon atom is formed?
1. Purchase alcohol 2.Verical alcohol 3.aldehyde 4.Ukton 5.Qarboxylic acid 49. Directly characteristic of oxidase reactions:
1. Cycelodine is restored to the water 2. Cyclood is turned on into the composition of the oxidated molecule 3. Calculation is oxidized to oxidation of hydrogen cleaved from the substrate 4. Recovery have an energy value 5. Recovery have a plastic value 50.What from the proposed substrates oxidizes in the cell easier and why?
1. Glucose 2. Silent acid 3. The partially oxidized carbon atoms 4. Suitable completely hydrogenated carbon atoms 51. Select aldosis:
1. Glucose 2.Rebosis of 3.Fructose 4. Galatosis 5. Select the spare forms of carbohydrates in a living organism:
1. Racket 2. Account 3. Glylogen 4.Galuric acid 5.Share 53. Select the most common monosaccharides in nature:
1.Tripes 2. 3.Tentose 4. Gexose 5.Geptosis 54.Select Aminosahara:
1. Beta-robosis 2. Glucosamine 3. Galaktoosamine 4. Aacetylgalactosamine 5. Select the oxidation products of monoshares:
1. Glucoso-6-phosphate 2. Gliding (Aldon) Acids 3. Glikuronic (URON) Acid 4. Glycosides 5. FIRS 56.Select disaccharides:
1. Maltosis 2. Racket 3. Glylogen 4.Shairoz 5.Lotosis 57.Select homopolysaccharides:
1. Stacked 2. Saleloose 3. Glylogen 4. Detail 5. Lotosis 58. Select which monosachara is formed during lactose hydrolysis:
1. Beta-D- Galactosis 2. Falph-Dzhalucosis 3. Falph-Dutoff 4. Falifa-D-galactose 5. Falifa-Dzoxiribosis 59. Select what is characteristic of cellulose:
1. The standard, vegetable polysaccharide 2.structural unit is the beta-diablication 3. Overcome for normal nutrition, is a potential substance 4. -Wed carbohydrate man. 5. Different in the gastrointestinal tract 60. Select carbohydrate derivatives included in the Mural:
1.N-acetylglucosamine 2.N-acetylmoramic acid 3. Glucosamine 4. Glucuroic acid 5.Ribulose-5-phosphate 61.Select from the following statements correct: amino acids are ...
1. Compounds containing in the molecule at the same time amino and hydroxy group 2. Compounds containing hydroxyl and carboxyl groups 3. The carboxylic acid derivatives in the radical of which hydrogen is substituted on the amino group 4. Compounds containing in the oxo molecule and carboxyl group 5. Connections containing Oxy and aldehyde groups 62. How class classified amino acids?
1. Accordingly, the chemical nature of the radical 2.After the physicochemical properties of 3. by the number of functional groups 4. In the degree of unsaturation of 5. In the nature of additional functional groups 63. Select the aromatic amino acid:
1. Glycine 2. Serine 3. Glutamine 4.Phenylalanine 5.Metionine 64.Select the amino acid exhibiting acid properties:
1.Lescin 2.Tripotofan 3. Glycine 4.Hlutamin 5.Line 65.Select the primary amino acid:
1. Serine 2.Lizin 3.Alin 4.Hlutamin 5.Triptopan 66.Select purine nitrogenous bases:
1.Timin 2.Adenin 3.Guananine 4.Surezil 5.Sitozin 67. Select pyrimidine nitrogen bases:
1.URAURCIL 2.Timin 3.Sitozin 4.Adenin 5.Guanin 68.Select the components of the nucleoside:
1.Purine nitrogen bases 2.Pyrimidine nitrogenous bases 3. Releases 4. Sexicity 5. Phosphoric acid 69. Here the structural components of nucleotides:
1.Purine nitrous bases 2. Pyrimidine nitrogenous bases 3. POBUS 4. Sexicity 5. Phosphoric acid 70.Dell a distinguishing feature of DNA:
1. Found by one polynucleotide chain 2. Educated by two polynucleotide chains 3. Conducts ribosa 4. Low deoxyribose 5. Suitable Uracil 6. Suitable Timin 71.Select the washesy lipids:
1.Nextral fats 2.TRiacyl glycerolines 3.Pospholipids 4.sFingomines Sinteroids 72. Select unsaturated fatty acids:
1.Palmitis 2.Shearine 3. olenovaya 4.INOLOLE 5.Arachidone 73.Tell, the characteristic composition of neutral fats:
1.Mericyl alcohol + palmitic acid 2. Glycerin + oil acid 3.Sfingosine + phosphoric acid 4. Glycerin + highest carboxylic acid + phosphoric acid 5. Glycerin + higher carboxylic acids 74.Select what function phospholipids in the human body are performed:
1. Regulatory 2. Protective 3. Design 4. Energy 75.Select glycolipids:
1. Fosphatidylcholine 2. Cebrosida 3.Sfinomyelin 4.Sulfatide 5. Gangliosides
Answers to test tasks
8.4 List of practical skills and tasks (in full) required for delivery 1. The ability to classify organic compounds on the structure of the carbon skeleton and by 2. The ability to draw up formulas by names and call on the structural formula typical representatives of biologically important substances and medicines.3. The ability to allocate functional groups, acidic and main centers, conjugate and aromatic fragments in molecules to determine chemical behavior 4. Ability to predict the direction and result of the chemical transformations of organic 5. possessing the skills of independent work with educational, scientific and reference literature; Search and make generalizing conclusions.
6. Having a chemical dishes handling skills.
7. Having the skills of safe work in the chemical laboratory and the ability to handle caustic, poisonous, volatile organic compounds, working with burners, alcohol and electric heating devices.
1. The subject and tasks of bioorganic chemistry. Meaning in medical education.
2. Elementary composition of organic compounds, as the cause of their compliance with biological processes.
3. Classification of organic compounds. Classes, general formulas, funkonal groups, individual representatives.
4. Nomenclature of organic compounds. Trivial names. Replacement nomenclature of the Jew.
5. The main functional groups. Rhodonachable structure. Deputy. Seniority of groups, deputies. Names of functional groups and substituents as a prefix and end.
6. Theoretical foundations of the structure of organic compounds. Theory A.M. Butlerova.
Structural formulas. Structural isomeria. Isomers chains and positions.
7. Spatial structure of organic compounds. Stereochemical formulas.
Molecular models. The most important concepts in stereo-configurations and conformation of organic molecules.
8. Conformations of open chains - obscured, inhibited, beveled. Energy and reactivity of various conformations.
9. Conformations of cycles on the example of cyclohexane (chair and bath). Axial and equatorial connections.
10. The influence of atoms in organic compound molecules. His reasons, types of manifestation. Effect on the reaction capacity of molecules.
11. Conditions. Conjugated systems, conjugate connections. Pyi pairing in dienes. Energy of pairing. Stability of conjugate systems (vitamin A).
12. Conditions in the Arena (PI-PI Course). Aromaticity. Hyukkel rule. Benzole, Naphthalene, Fenantrene. The reactivity of the benzene ring.
13. Conditions in heterocycles (p-pp and pi-pi pairing on the example of pyrrole and pyridine).
Stability of heterocycles - biological significance On the example of tetrapyrrol compounds.
14. Reolarization of connections. The reasons. Polarization in alcohols, phenols, carbonyl compounds, thiola. Effect on the reaction capacity of molecules. \\ 15.Electronic effects. Inductive effect in molecules containing, sigma-links. Inductive effect sign.
16.Merry effect in open circuits with conjugate PI bonds on the example of butadiene-1,3.
17.Merry effect in aromatic compounds.
18.Electronic and electron substituents.
19. Officers of the I-go and II. Rule of orientation in the benzene ring.
20.Citness and basicity of organic compounds. Acids and bases of Brandstay Lowry.
Acid-major pairs are conjugated acids and again. KA and PKA - quantitative characteristics of the acidity of organic compounds. The value of acidity for the functional activity of organic molecules.
21.Citness of various classes of organic compounds. The factors that determine the acidity of organic compounds are the electronegability of the non-metallium atom associated with hydrogen, the polarizability of the non-metal atom, the nature of the radical associated with the nonmetal atom.
22.ganic grounds. Amines. Cause of basicity. The effect of radical on the basicity of aliphatic and aromatic amines.
23. Classification of the reactions of organic compounds by their mechanism. The concepts of homolitic and heterolitic reactions.
24. Recovery on the radical type of alkanes. Free-radical oxidation in living organisms. Active forms of oxygen.
25.Electrophilic attachment in alkenes. The formation of PI complexes, carboations. Hydration reactions, hydrogenation.
26.Electrophilic replacement in the aromatic core. The formation of intermediate sigmacomplexes. Benzol bromination reaction.
27.Nextoophilic replacement of alcohols. Dehydration reactions, oxidation of primary and secondary alcohols, ethers formation.
28.Nextoophilic connection in carbonyl compounds. Biologically important aldehyde reactions: oxidation, the formation of semi-acetals when interacting with alcohols.
29.Notoophilic replacement in carboxylic acids. Biologically important carboxylic acid reactions.
30.Oc acidification of organic compounds, biological significance. The degree of carbon oxidation in organic molecules. Oxidation of different classes of organic compounds.
31. Energy oxidation. Oxidase reactions.
32.Nenergetic oxidation. Oxygenase reactions.
33.Rol free-radical oxidation in the bactericidal action of phagocytic cells.
34. Restoration of organic compounds. Biological significance.
35. Polyifunctional compounds. Multiatomic alcohols - ethylene glycol, glycerin, xylitis, sorbitol, inosit. Biological significance. Biologists are important glycerol reactions - oxidation, formation of esters.
36. Double dicarboxylic acids: oxal, malonic, amber, glutar.
Transformation of succinic acid into fumarois - an example of biological dehydrogenation.
37.amines. Classification:
By the nature of the radical (aliphatic and aromatic); - by the amount of radicals (primary, secondary, tertiary, quaternary ammonium bases); - by the amount of amino groups (mono- and diamine-). Diamine: Pretssin and Cadaver.
38.Getherofunctional compounds. Definition. Examples. Features of manifestation of chemical properties.
39.Nicompirts: ethanolamine, choline, acetylcholine. Biological significance.
40. Oxycycles. Definition. General formula. Classification. Nomenclature. Isomeria.
Representatives of monocarbonic oxycoslot: dairy, beta-hydroxymalas, gamma-xymasalya;
dicarboxyls: Apple, Wine; tricarboxyls: lemon; Aromatic: Salicyl.
41. Chemical properties of oxic acid: for carboxyl, by a suites group, dehydration reaction in alpha, beta and gamma-isomers, distinction of reaction products (lactides, unsaturated acids, lactones).
42.Steroisomeria. Enantiomers and diastereomers. The chirality of organic compound molecules as the cause of the optical isomerism.
43.Nantiomers with one center of chirality (lactic acid). Absolute and relative configuration of enantiomers. Oxyxic acid key. D and L glycerin aldehyde. D and L isomers.
Racemates.
44.Nantiomers with several chirality centers. Wine and meson acids.
45.Steroisomeria and biological activity of stereoisomers.
46. \u200b\u200bCentral and trans isomeria on the example of fumarone and maleic acids.
47.Oxiscovers. Definition. Biologically important representatives: peer-grade, acetoxus, oxhelevoacetic. Ketoenol tautomeria on the example of pyruogradic acid.
48.Amino acids. Definition. General formula. Isomers of the position of amino group (alpha-, beta, gamma-). The biological value of alphaaminoxot. Representatives of beta, gamma, and other isomers (betaminopropionic, gammaamic-oil, epsilonamicapron). The reaction of the dehydration of gamma-isomers with the formation of cyclic lactones.
49.Getherofunctional derivatives of benzene, as the basis of medicines. Derivatives of P-aminobenzoic acid - PABK (folic acid, anesthesine). PABK antagonists derivatives of sulfanyl acid (sulfonamides - streptocid).
50.Getherofunctional derivatives of benzene - drugs. Raminofenol derivatives (paracetamol), salicylic acid derivatives (acetylsalicylic acid). Raminosalcyl Acid - Pask.
51.Biologically important heterocycles. Definition. Classification. Features of the structure and properties: conjugation, aromatic, stability, reactivity. Biological significance.
52.Thisted heterocycles with one heteroatom and their derivatives. Pyrrol (Porphine, Porphyrins, Gem), Furan (drugs), thiophene (biotin).
53.The heterocycles with two heteroatoms and their derivatives. Pirazole (5-power produced), imidazole (histidine), thiazole (vitamin B1-thiamine).
54.Stended heterocycles with one heteroatom and their derivatives. Pyridine (Nicotinic Acid is participation in oxidative reaction reactions, vitamin B6-pyridoxal), quinoline (5-nct), isoquinoline (alkalloids).
55.tened heterocycles with two heteroatoms. Pyrimidine (cytosin, Uracil, Timin).
56.Conned heterocycles. Purin (Adenin, Guanin). Pyrine oxidation products hypoxanthine, xanthin, urinary acid).
57.Talloids. Definition and general characteristics. The structure of nicotine and caffeine.
58.Glip. Definition. Classification. Functions of carbohydrates in living organisms.
59.monoshara. Definition. Classification. Representatives.
60.Tentoses. Representatives - robosis of the deoxyribosis. Building, open and cyclic formulas. Biological significance.
61.Gexose. Aldoz and ketosis. Representatives.
62. Open formulas of monosachar. Definition of stereochemical configuration. Biological configuration of monosachar.
63. Education of cyclic forms of monosacharov. Glycosidoid hydroxyl. Alpha and Betanetomiers. The formulas of Heuors.
64.Production of monosacharov. Phosphoric esters, glyacon and glycuronic acids, aminosahara and their acetyl derivatives.
65. Maltosis. Composition, structure, hydrolysis and value.
66.Lactose. Synonym. Composition, structure, hydrolysis and value.
67.Asaches. Synonyms. Composition, structure, hydrolysis and value.
68.Gomopolisaccharides. Representatives. Starch, structure, properties, hydrolysis products, value.
69.glyogen. Building, role in an animal body.
70.Fillet. Building, role in plants, value for humans.
72.Getheropolisaccharides. Synonyms. Functions. Representatives. Feature structure-dimeric links, composition. 1,3- and 1,4-glycoside ties.
73.galuronic acid. Composition, structure, properties, value in the body.
74. Chondroitin Sulfate. Composition, structure, value in the body.
75.Muramin. Composition, value.
76. Falia amino acids. Definition. General formula. Nomenclature. Classification. Separate representatives. Stereoisomeria.
77.Chemical properties of alphaaminoxot. Amphoteriness, decarboxylation, deamination reaction, hydroxylation in the radical, the formation of peptide communication.
78.Peptides. Individual peptides. Biological role.
79.Lork. Protein functions. Structure levels.
80.Azotic bases of nucleic acids - purines and pyrimidines. Modified nitrogen bases - antimetabolites (fluoruracyl, mercaptopurine).
81.Noteosides. Nucleosides antibiotics. Nucleotides. Mononucleotides in the composition of nucleic acids and free nucleotides - coherents.
82.Nokleinic acids. DNA and RNA. Biological significance. The formation of phosphodieter ties between mononucleotides. Levels of the structure of nucleic acids.
83.Lipids. Definition. Biological role. Classification.
84. High carboxylic acids - saturated (palmitic, stearin) and unsaturated (olein, linoleic, linolen and arachidon).
85.Nextral fats - acylglycerin. Building, value. Animals and vegetable fats.
Hydrolysis of fats - products, meaning. Hydrogenation of vegetable oils, artificial fats.
86. Glycerofospholipids. Building: phosphatide acid and nitrogenous bases.
Phosphatidylcholine.
87.Sfingolipids. Structure. Sphinosin. Sfigomyelin.
88.Steroids. Cholesterol - structure, value, derivatives: bile acids and steroid hormones.
89.Things and terpenoids. Building and biological significance. Representatives.
90. Healthy vitamins. General characteristics.
91. Means for anesthesia. Diethyl ether. Chloroform. Value.
92. Medicines for metabolic processes stimulants.
93. Sulfonamides, structure, meaning. White streptocid.
94. Antibiotics.
95. Anti-inflammatory and antipyretic means. Parasetamol. Structure. Value.
96. Antioxidants. Characteristic. Value.
96. Tiol. Antidotes.
97. Anticoagulants. Characteristic. Value.
98. Barbiturates. Characteristic.
99. Analgesics. H. Examples. Acetylsalicylic acid (aspirin).
100. Antiseptics. Value. Examples. Fucylin. Characteristic. Value.
101. Antiviral drugs.
102. Digestons.
103. Means for parenteral nutrition.
104. PABK, PASK. Structure. Characteristic. Value.
105. iodoform. Xeroform.
106. Polyglyukin. Characteristic. Value 107.Formal. Characteristic. Value.
108. Xylitis, sorbitol. Building, value.
109. Resorcin. Building, value.
110. Atropine. Value.
111. Caffeine. Structure. Meaning 113. Furacilin. Furazolidon. Characteristic. Description.
114. GABA, GOM, AMERIC Acid .. Building. Value.
115. Nicotinic acid. Building, value
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Bioorganic chemistry, studies the link between the structure of organic substances and their biological functions, using mainly methods of organic and physical chemistry, as well as physics and mathematics. Bioorganic chemistry fully covers the chemistry of natural compounds and partially intersects with biochemistry and molecular biology. The objects of its study are biologically important natural compounds - mainly biopolymers (proteins, nucleic acids, polysaccharides and mixed biopolymers) and low molecular weight biologically active substances - vitamins, hormones, antibiotics, toxins, and so on, as well as synthetic analogues of natural compounds, drugs, Pesticides, etc.
Bioorganic chemistry was formed as an independent area in the 2nd half of the 20th century at the junction of biochemistry and organic chemistry based on the traditional chemistry of natural compounds. Its becoming is associated with the names of L. Poling (the discovery of the α-helix and β-structure as the main elements of the spatial structure of the polypeptide chain in proteins), A. Todd (clarification of the chemical structure of nucleotides and the first synthesis of dinucleotide), F. Senger (Development of the Amino Acid Definition Mode sequences in proteins and decoding with its help of the primary insulin structure), V. du Vino (allocation, structure of structure and chemical synthesis of peptide hormones - oxytocin and vasopressin), D. Barton and V. Pravoga (conformational analysis), R. Woodvord (full chemical synthesis of many complex natural compounds, including reserpine, chlorophyll, vitamin B 12), etc.; In the USSR, the work of N. D. Zelinsky, A. N. Belozersky, I. N. Nazarova, N. A. Preobrazhensky, and others were played a huge role. Initiator of research on bioorganic chemistry in the USSR in the early 1960s was MM. Shemyakin. In particular, work was launched (subsequently received widespread development) on the study of cyclic depotides performing the function of ionophos. The leader of domestic bioorganic chemistry in the 1970-80s was Yu.A. Ovchinnikov, under the leadership of which the structure of dozens of proteins was established, including membrane (for the first time) - bacterioriopcin and visual Rhodopsin bull.
The main directions of bioorganic chemistry include:
1. Development of methods for isolating and cleaning natural compounds. At the same time, the specific biological function of the studied substance is often used to control the degree of purification (for example, the purity of the antibiotic is controlled by its antimicrobial activity, hormone - by its influence on a certain biological process, and so on). In the separation of complex natural mixtures, highly efficient liquid chromatography and electrophoresis are often used. Since the end of the 20th century, instead of searching and sewing individual components, a total screening of biological samples is carried out to the maximum possible number of components of a particular connection class (see proteomics).
2. Determination of the structure of studied substances. Under the structure, not only the establishment of nature and the order of communication of atoms in the molecule, but also their spatial location. For this purpose, various methods are used, primarily chemical (hydrolysis, oxidative splitting, treatment with specific reagents), allowing more simple substances with a known structure, along which the structure of the source substance is reconstructed. Automatic devices are widely used, providing a rapid solution of standard problems, especially in chemistry of proteins and nucleic acids: analyzers for the quantitative determination of amino acid and nucleotide composition and sequenters to determine the sequence of amino acid residues in proteins and nucleotides in nucleic acids. An important role in the study of the structure of biopolymers is played by enzymes, especially those that specifically cleave them according to strictly defined bonds (for example, proteinases, catalyzing peptide bonding reactions on glutamic acid residues, proline, arginine and lysine, or restrictions, specifically cleaving phosphodiester communications in polynucleotides ). Information about the structure of natural compounds is also obtained by physical methods Studies - mainly mass spectrometry, nuclear magnetic resonance and optical spectroscopy. Improving the efficiency of chemical and physical methods is achieved due to the simultaneous analysis of not only natural compounds, but also their derivatives containing characteristic, specially introduced groupings and labeled atoms (for example, by growing bacteria - producers of one or another compound on an environment containing precursors of this compound enriched stable or radioactive isotopes). The accuracy of the data obtained in the study of complex proteins is significantly increased by simultaneously studying the structure of the respective genes. The spatial structure of molecules and their analogues in the crystalline state is investigated by X-ray analysis. Resolution in some cases reaches values \u200b\u200bless than 0.1 nm. For solutions, the NMR method is most informative in combination with theoretical conformational analysis. Extension information is given optical spectral analysis methods (electronic and fluorescent spectra, spectra of circular dichroism, etc.).
3. Synthesis of both the natural compounds themselves and their analogues. In many cases, chemical or chemical-enzymatic synthesis is the only way to obtain the desired substance in large (preparative) quantities. For relatively simple low molecular weight compounds, the counter synthesis serves as an important criterion for the correctness of a previously defined structure. Automatic protein and polynucleotide synthesizers have been created, which can significantly reduce the synthesis time; With their help, a series of proteins and polynucleotides containing several hundred monomer units are synthesized. Chemical synthesis is a basic way to obtain non-drug drugs. In the case of natural substances, he often complements biosynthesis or competes with it.
4. The establishment of a cellular and molecular target to which the action of a biologically active substance is directed, finding out the chemical mechanism of its interaction with a living cell and its components. Understanding the molecular mechanism of action is necessary for productive use of biomolecules, with their often extremely high activity (for example, toxins), as instruments for researching biological systems; It serves as the basis for the directional synthesis of new, practically important substances with predetermined properties. In some cases (for example, in the study of peptides affecting the activity of the nervous system), the substances obtained in this way have many times reinforced compared with the original natural prototype, modified in the desired activity.
Bioorganic chemistry is closely related to the solution of practical problems of medicine and agriculture (Preparation of vitamins, hormones, antibiotics and other medicines, plant growth stimulants, animal behavior regulators, including insects), chemical, food and microbiological industries. As a result of the combination of methods of bioorganic chemistry and genetic engineering, it became possible a practical solution to the problem of industrial production of complex, biologically important substances of protein-peptide nature, including such high molecular weight, as insulin of a person, α-, β- and γ-interferons, human growth hormone.
Lit.: Digid, Penny K. Bioorganic Chemistry. M., 1983; Ovchinnikov Yu. A. Bioorganic chemistry. M., 1996.