Benzoyl-CoA explained

Benzoyl-CoA is the thioester derived from benzoic acid and coenzyme A. The term benzoyl-CoA also include diverse conjugates of coenzyme A and aromatic carboxylic acids. Benzoate, vanillin, anthranilic acid, 4-ethylphenol, p-cresol, phenol, aniline, terephthalic acid, [3-hydroxybenzoic acid], and phenylalanine are all metabolized to benzoyl-CoA. Additionally,cinnamic acid, p-coumaric acid, ferulic acid, toluene, caffeic acid, benzyl alcohol, and mandelic acid are suspected to be processed similarly.

As substrate for reductases

Benzoyl-CoA is a substrate for diverse reductases:[1] 4-hydroxybenzoyl-CoA reductase, benzoyl-CoA reductase, benzoyl-CoA 3-monooxygenase, benzoate-CoA ligase, 2alpha-hydroxytaxane 2-O-benzoyltransferase, anthranilate N-benzoyltransferase, biphenyl synthase, glycine N-benzoyltransferase, ornithine N-benzoyltransferase and phenylglyoxylate dehydrogenase (acylating). Benzoyl-CoA reductase converts benzoyl-CoA to cyclohex-1,5-diene-1-carbonyl-CoA, which is susceptible to hydrolysis, eventually giving acetyl coenzyme A. In this way, many aromatic compounds are biodegraded.

As a benzoyl donor

Benzoyl-CoA is a benzoyl transfer agent for the biosynthesis of hippuric acid. Benzoyl-CoA is a substrate in the formation of xanthonoids in Hypericum androsaemum by benzophenone synthase, condensing a molecule of benzoyl-CoA with three malonyl-CoA, yielding to 2,4,6-trihydroxybenzophenone. This intermediate is subsequently converted by a benzophenone 3′-hydroxylase, a cytochrome P450 monooxygenase, leading to the formation of 2,3′,4,6-tetrahydroxybenzophenone.[2]

Benzoyl-CoA is a substrate of benzoyl-CoA reductase. This enzyme is responsible in part for the reductive dearomatization of aryl compounds mediated by bacteria under anaerobic conditions.[3]

Notes and References

  1. 24767428 . 2014 . Porter . A. W. . Young . L. Y. . Benzoyl-CoA, a Universal Biomarker for Anaerobic Degradation of Aromatic Compounds . Advances in Applied Microbiology . 88 . 167–203 . 10.1016/B978-0-12-800260-5.00005-X . 978-0-12-800260-5 .
  2. https://archive.today/20120917104009/http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T36-3RSNBYV-7&_user=10&_coverDate=12/29/1997&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=698ce0fcabfd07c74909356df6166c31 Alternative pathways of xanthone biosynthesis in cell cultures of Hypericum androsaemum L. Werner Schmidt and Ludger Beerhues, FEBS Letters, Volume 420, Issues 2-3, 29 December 1997, Pages 143-146
  3. Matthias Boll, Georg Fuchs, Johann Heider "Anaerobic oxidation of aromatic compounds and hydrocarbons" Current Opinion in Chemical Biology 2002 Volume 6, pp. 604–611.