Phenylacetyl-CoA explained

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-[[(2''R'')-4-[[[(2''R'',3''S'',4''R'',5''R'')-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]

Notes and References

  1. Web site: Phenylacetyl-CoA. PubChem. pubchem.ncbi.nlm.nih.gov. en.
  2. Phenylacetyl-Coenzyme A Is the True Inducer of the Phenylacetic Acid Catabolism Pathway in Pseudomonas putida U . García . Belén . Olivera . Elías R. . October 2000 . 4575–4578 . 11010921 . 92347. Miñambres . Baltasar . Carnicero . David . Muñiz . Carmen . Naharro . Germán . Luengo . José M.. Applied and Environmental Microbiology. 66. 10. 10.1128/aem.66.10.4575-4578.2000. 2000ApEnM..66.4575G .
  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. en. 262. 2. 507–515. 10.1046/j.1432-1327.1999.00399.x. 10336636. 1432-1033.
  4. Web site: Human Metabolome Database: Showing metabocard for Phenylacetyl-CoA (HMDB0006503). www.hmdb.ca. 2019-11-06.