Phenylacetyl-CoA

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Phenylacetyl-CoA
Phenylacetyl-CoA.svg
Chemical structure of phenylacetyl-CoA
Names
Preferred IUPAC name
O1-{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-[(3R)-3-hydroxy-2-methyl-4-{[3-oxo-3-({2-[(phenylacetyl)sulfanyl]ethyl}amino)propyl]amino}-4-oxobutyl] dihydrogen diphosphate
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
KEGG
  • InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24+,28-/m1/s1
    Key: ZIGIFDRJFZYEEQ-CECATXLMSA-N
  • CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCSC(=O)CC4=CC=CC=C4)O
Properties
C29H42N7O17P3S
Molar mass 885.67 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phenylacetyl-CoA (C29H42N7O17P3S) is a form of acetyl-CoA formed from the condensation of the thiol group from coenzyme A with the carboxyl group of phenylacetic acid.[1][2]

Its molecular-weight is 885.7 g/mol. and IUPAC name is S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] 2-phenylethanethioate. It is formed via the actions of Phenylacetate—CoA ligase.[3]

Phenylacetyl-CoA is often produced via the reduction of ATP to AMP and the conversion of phenylacetate and CoA to diphosphate and Phenylacetyl-CoA.

ATP + phenylacetate + CoA → AMP + diphosphate + phenylacetyl-CoA

This reaction is catalyzed by phenylacetate-CoA ligase.

Phenylacetyl-CoA combines with water and quinone to produce phenylglyoxylyl-CoA and quinol via a phenylacetyl-CoA dehydrogenase reaction acting as an oxidoreductase.

Phenylacetyl-CoA inhibits choline acetyltransferase acting as a neurotoxin. It competes with acetyl-CoA.[4]

References[edit]

  1. ^ PubChem. "Phenylacetyl-CoA". pubchem.ncbi.nlm.nih.gov.
  2. ^ García, Belén; Olivera, Elías R.; Miñambres, Baltasar; Carnicero, David; Muñiz, Carmen; Naharro, Germán; Luengo, José M. (October 2000). "Phenylacetyl-Coenzyme A Is the True Inducer of the Phenylacetic Acid Catabolism Pathway in Pseudomonas putida U". Applied and Environmental Microbiology. 66 (10): 4575–4578. Bibcode:2000ApEnM..66.4575G. doi:10.1128/aem.66.10.4575-4578.2000. PMC 92347. PMID 11010921.
  3. ^ Rhee, Sung-Keun; Fuchs, Georg (1999). "Phenylacetyl-CoA:acceptor oxidoreductase, a membrane-bound molybdenum–iron–sulfur enzyme involved in anaerobic metabolism of phenylalanine in the denitrifying bacterium Thauera aromatica". European Journal of Biochemistry. 262 (2): 507–515. doi:10.1046/j.1432-1327.1999.00399.x. ISSN 1432-1033. PMID 10336636.
  4. ^ "Human Metabolome Database: Showing metabocard for Phenylacetyl-CoA (HMDB0006503)". www.hmdb.ca. Retrieved 2019-11-06.