Coenzyme A ( coenzyme A , CoA , CoA , HSKoA ) - coenzyme of acetylation ; one of the most important coenzymes involved in the transfer reactions of acyl groups in the synthesis and oxidation of fatty acids and the oxidation of pyruvate in the citric acid cycle . [one]
| Coenzyme A | |
|---|---|
 | |
 | |
| General | |
| Systematic name | [(2R, 3S, 4R, 5R) -5- (6-aminopurin-9-yl) -4-hydroxy-3-phosphonooxyoxolan-2-yl] methyl diphosphate - [(3R) -3-hydroxy-2, 2-dimethyl-4-oxo-4 - [[3-oxo-3- (2-sulfanylethylamino) propyl] amino] butoxy] |
| Traditional names | coenzyme A |
| Chem. formula | C 21 H 36 N 7 O 16 P 3 S |
| Physical properties | |
| Molar mass | 767.534 ± 0.031 g / mol |
| Classification | |
| Reg. CAS number | 85-61-0 |
| PubChem | |
| Reg. EINECS number | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
Content
- 1 Building
- 2 Biosynthesis
- 3 Biochemical role
- 4 History of the discovery
- 5 List of acyl-CoA
- 6 See also
- 7 notes
- 8 Literature
Building
The coenzyme A molecule consists of an adenylic acid residue (1) linked by a pyrophosphate group (2) to a pantoic acid residue (3), which in turn is linked by an amide bond to the amino acid β- alanine (4) (these two groups represent a pantothenic acid residue ), connected by an amide bond with the residue of β-mercaptoethanolamine (5).
Biosynthesis
Coenzyme A is synthesized in five steps from pantothenic acid ( vitamin B 5 ) and cysteine :
- Pantothenic acid is phosphorylated to 4'-phosphopantothenate using pantothenate kinase enzyme
- Cysteine binds to 4'-phosphopantothenate using the enzyme phosphopantotenoylcysteine synthetase to form 4'-phospho-N-pantothenoylcysteine
- 4'-phospho-N-pantothenoylcysteine is decarboxylated to form 4'-phosphopantothein using the enzyme phosphopantotenoylcysteine decarboxylase
- 4'-phosphopantothein with adenylic acid forms dephospho-CoA under the action of the enzyme phosphopantothein adenyl transferase
- Finally, dephospho-CoA phosphorylates ATP to coenzyme A using the dephosphocoenzyme kinase enzyme.
Biochemical role
A number of biochemical reactions underlying the oxidation and synthesis of fatty acids , the biosynthesis of fats, and the oxidative transformations of carbohydrate decomposition products are associated with CoA. In all cases, CoA acts as an intermediate linking and transferring acid residues to other substances. In this case, the acid residues in the composition of the compound with CoA undergo certain transformations, or are transferred without change to certain metabolites.
Discovery History
Coenzyme was first isolated from the liver of a pigeon in 1947 by F. Lipman [2] . The structure of coenzyme A was determined in the early 1950s by F. Linen at the Lister Institute in London. The complete synthesis of CoA was carried out in 1961 by H. Quran .
Acyl CoA List
Various acyl derivatives of coenzyme A were isolated and identified from natural compounds:
Acyl-CoA from carboxylic acids:
- Acetyl-CoA
- Propionyl CoA
- Acetoacetyl-CoA
- Kumarol-CoA
- Butyryl-CoA
Acyl-CoA from dicarboxylic acids:
- Malonil-CoA
- Succinyl CoA
- Hydroxymethylglutaryl-CoA
- Pimenil-CoA
Acyl-CoA from carbocyclic acids:
- Benzoyl CoA
- Phenylacetyl-CoA
There are also a variety of acyl-CoA fatty acids that play a large role as substrates for lipid synthesis reactions.
See also
- Vitamin B 5
Notes
- ↑ Ovchinnikov Yu. A. Bioorganic chemistry / Yu. A. Ovchinnikov. - M .: Education, 1987 .-- 815 p., Ill.
- ↑ Baddiley , J .; Thain, EM; Novelli, GD; Lipmann, F. Structure of Coenzyme A (English) // Nature : journal. - 1953. - Vol. 171 , no. 4341 . - P. 76 . - DOI : 10.1038 / 171076a0 .
Literature
- Filippovich, Yu. B. Fundamentals of biochemistry: Textbook. for chem. and biol. specialist. ped University and in-to / Yu. B. Filippovich. - 4th ed., Revised. and add. - M .: "Agar", 1999. - 512 p., Ill.
- Berezov, T. T. Biological chemistry: Textbook / T. T. Berezov, B. F. Korovkin. - 3rd ed., Revised. and add. - M .: Medicine, 1998 .-- 704 p., Ill.
- Ovchinnikov, Yu. A. Bioorganic chemistry / Yu. A. Ovchinnikov. - M .: Education, 1987 .-- 815 p., Ill.
- Plemenkov, V.V. Introduction to the chemistry of natural compounds / V.V. Plemenkov. - Kazan: KSU, 2001 .-- 376 p.