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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 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
- (2014). "Benzoyl-CoA, a Universal Biomarker for Anaerobic Degradation of Aromatic Compounds". Advances in Applied Microbiology.
- 10.1016/S0014-5793(97)01507-X
- 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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