TASHKENT MEDICAL ACADEMY Department of Bioorganic and Biological Chemistry Bioorganic chemistry I COURSE Subject:  -Amino acids. Classification and chemical.

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Presentation transcript:

TASHKENT MEDICAL ACADEMY Department of Bioorganic and Biological Chemistry Bioorganic chemistry I COURSE Subject:  -Amino acids. Classification and chemical properties. LECTURE №10 LECTURER : PROFESSOR A.D.DZHURAEV

PURPOSE OF LECTURES: Form of knowledge of the structure and properties of the most important  - amino acids and the chemical basis of the structural organization of the protein molecules for further study of the biological functions of proteins at the molecular level.

The questions of: Classification of  - amino acids Stereoisomers  - amino acids The acid-base properties of  - amino acids Methods for producing  - amino acids Reaction at the carboxyl group  - amino acids Reaction of amino  - amino acids

Classification of amino acids A. The chemical nature of the radical divided into 1. aliphatic 2. aromatic 3. heterocyclic. B. the number of COOH and NH2 groups are divided into 1. neutral 2. basic 3. sour

NH 2 –СН 2 – СООН - neutral NH 2 – (CH 2 ) 4 –CH(NH2)-COOH – primary НООС –(CH 2 ) 2 - CH(NH 2 )-COOH – sour essential amino acids – valine, leucine, isoleucine, phenylalanine, threonine, methionine, tryptophan, lysine

Methods for producing amino acids out of the body 1. Cyanohydrin synthesis (or reaction-Zelinsky Stadnikova)

2. Ammonolysis-halocarboxylic acids R CH COOH Br NH 3 R CH COOH NH 2  excess NH 4 Br -

Synthesis of amino acids within the body I. Reductive amination C H 2 C COOH O H 2 CHOOC + NH 3  ketoglutaric acid NAD H NAD +  glutamic acid H 2 O + CH H 2 C COOH NH 2 H 2 CHOOC

2. Transamination (transamination ) enzyme transaminase К + pyridoxal phosphate acetic acid oxalate a-glutamic acid a-ketoglutaric acid aspartic acid

II. Chemical Properties 1. Acid-base properties.

EDUCATION BIPOLAR ION cation form bipolar ion anion form highly acidic environment strongly alkaline

2. Reaction of the carboxyl group The formation of salts. copper internal complex glycine

The formation of esters methyl ester of a- amino acids

The formation of halides or

The decarboxylation CH 2 HO CH COOH NH 2 CO 2 - CH 2 HO CH 2 NH 2 serine kolamin

3. Reaction of amino The formation of N-acyl derivatives :

Interaction with 2,4 - dinitrofluorobenzene? (Sanger reagent) + O 2 N NO 2 F H 2 N CH COOH R N CH COOH R NO 2 O 2 N H + - HO - HF DNF connection a-amino acids

Interaction with phenylthio isocyanate cyclization feniltiogidantoin a-amino acids

The deamination. aspartase oxalate oxidase α - keto acid α - hydroxy acid Van Slyke reaction

Reaction with aldehydes. R CH COOH NH 2 R CHCOOH NHCH 2 OH + C O H H C O H R' + - R CHCOOH NCHR' H 2 O R CH COOH NH 2 Schiff base N-hydroxymethyl a-amino acids