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general/thioesters-of-coenzyme-a

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Benzoyl-CoA

Benzoyl-CoA

S-Benzoate coenzyme A 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 processed anaerobically to the cyclohexadiene derivative.

Benzoyl-CoA is a substrate for diverse reductases: 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.

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.

References

References

  1. (2014). "Benzoyl-CoA, a Universal Biomarker for Anaerobic Degradation of Aromatic Compounds". Advances in Applied Microbiology.
  2. 10.1016/S0014-5793(97)01507-X
  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. {{doi. 10.1016/S1367-5931(02)00375-7
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