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Coenzyme A

Identifiers
CAS Number	85-61-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15346
ChEMBL	ChEMBL1213327
ChemSpider	6557
DrugBank	DB01992
ECHA InfoCard	100.001.472
KEGG	C00010
MeSH	Coenzyme+A
PubChem CID	6816
UNII	SAA04E81UX
InChI InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16?,20-/m1/s1Key: RGJOEKWQDUBAIZ-DRCCLKDXSA-N InChI=1/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16?,20-/m1/s1Key: RGJOEKWQDUBAIZ-DRCCLKDXBU
SMILES O=C(NCCS)CCNC(=O)C(O)C(C)(C)COP(=O)(O)OP(=O)(O)OC3O(n2cnc1c(ncnc12)N)(O)3OP(=O)(O)O
Properties
Chemical formula	C21H36N7O16P3S
Molar mass	767.535
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is  ?) Infobox references

Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. All sequenced genomes encode enzymes that use coenzyme A as a substrate, and around 4% of cellular enzymes use it (or a thioester, such as acetyl-CoA) as a substrate. It is adapted from cysteamine, pantothenate, and adenosine triphosphate.

Biosynthesis

Coenzyme A is synthesized in a five-step process from pantothenate and cysteine:

1. Pantothenate (vitamin B₅) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK; CoaA; CoaX)
2. A cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC; CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC)
3. PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC)
4. 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD)
5. Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE).

Discovery of structure

The structure of co-enzyme A was defined in the early 1950s at the Lister Institute, London, together with other workers at Harvard Medical School and Massachusetts General Hospital.

Function

Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. It assists in transferring fatty acids from the cytoplasm to mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'.

Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier protein and formyltetrahydrofolate dehydrogenase.

List of coenzyme A-activated acyl groups

• Acetyl-CoA
• Propionyl-CoA
• Acetoacetyl-CoA
• Coumaroyl-CoA (used in flavonoid and stilbenoid biosynthesis)
• Acyl derived from dicarboxylic acids
  • Malonyl-CoA
  • Succinyl-CoA (used in heme biosynthesis)
  • Hydroxymethylglutaryl-CoA (used in isoprenoid biosynthesis)
  • Pimelyl-CoA (used in biotin biosynthesis)
  • fatty acyl-CoA (activated form of all fatty acids; only the CoA esters are substrates for important reactions such as mono-, di-, and triacylglycerol synthesis, carnitine palmitoyl transferase, and cholesterol esterification)
• Benzoyl CoA
• Phenylacetyl CoA
• Butyryl CoA

Additional images

• Coenzyme A

References

1. Matthew Daugherty, Boris Polanuyer, Michael Farrell, Michael Scholle, Athanasios Lykidis, Valérie de Crécy-Lagard and Andrei Osterman (2002). "Complete Reconstitution of the Human Coenzyme A Biosynthetic Pathway via Comparative Genomics". The Journal of Biological Chemistry. 277: 21431–21439. doi:10.1074/jbc.M201708200. PMID 11923312.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
2. Baddiley, J.; Thain, E. M.; Novelli, G. D.; Lipmann, F. (1953). "Structure of Coenzyme A". Nature. 171 (4341): 76. doi:10.1038/171076a0.
3. Elovson J, Vagelos PR (1968). "Acyl carrier protein. X. Acyl carrier protein synthetase". J. Biol. Chem. 243 (13): 3603–11. PMID 4872726. {{cite journal}}: Unknown parameter |month= ignored (help)
4. Strickland KC, Hoeferlin LA, Oleinik NV, Krupenko NI, Krupenko SA (2010). "Acyl carrier protein-specific 4'-phosphopantetheinyl transferase activates 10-formyltetrahydrofolate dehydrogenase". J. Biol. Chem. 285 (3): 1627–33. doi:10.1074/jbc.M109.080556. PMC 2804320. PMID 19933275. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)

Bibliography

• Karl Miller (1998). Beta Oxidation of Fatty Acids. Retrieved May 18, 2005.
• Charles Ophard (2003). Acetyl-CoA Crossroads. Retrieved May 18, 2005.
• Nelson, David L.; Cox, Michael M. (2005). Lehninger: Principles of Biochemistry (4th ed.). New York: W.H. Freeman. ISBN 0716743396.
• Overview of Fatty Acid Oxidation Reactions

• Coenzymes
• Metabolism
• Thiols