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Chemical Compound Review

AR-1L3753     [(2R,3S,4R)-5-(6-aminopurin- 9-yl)-4...

Synonyms: AC1L3U4G, 6756-74-7, benzoyl-coenzyme A, Coenzyme A, benzoyl-, Coenzyme A, S-benzoate
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Disease relevance of benzoyl-coenzyme A

  • Benzoyl-CoA reductase (BCR) from the bacterium Thauera aromatica catalyzes the two-electron reduction of benzoyl-CoA (BCoA) to a nonaromatic cyclic diene [1].
  • The recombinant enzyme expressed in E. coli has a pH optimum at 8.0, a k(cat) approximately 1.5 +/- 0.3 s(-1) and K(m) values of 0.42 mM and 0.40 mM for the N-deacylated taxoid and benzoyl-CoA, respectively [2].
  • A three-dimensional model of the N-terminal and C-terminal regions of BzdR, generated by comparison with the crystal structures of the SinR regulator from Bacillus subtilis and the shikimate kinase I protein from E. coli, strongly suggests that they contain the helix-turn-helix DNA-binding motif and the benzoyl-CoA binding groove, respectively [3].
  • Aerobic benzoyl-CoA catabolic pathway in Azoarcus evansii: studies on the non-oxygenolytic ring cleavage enzyme [4].
  • This work highlights that the major difference in anaerobic benzoate metabolism of facultative and strictly anaerobic bacteria is the reductive process for dearomatization of benzoyl-CoA [5].

High impact information on benzoyl-coenzyme A

  • To test this hypothesis, we generated transgenic petunia plants in which the expression of BPBT, the gene encoding the enzyme that uses benzoyl-CoA and benzyl alcohol to make benzylbenzoate, was reduced or eliminated [6].
  • The recombinant benzoyltransferase has a pH optimum of 8.0, K(m) values of 0.64 mM and 0.30 mM for the taxoid substrate and benzoyl-CoA, respectively, and is apparently regiospecific for acylation of the 2alpha-hydroxyl group of the functionalized taxane nucleus [7].
  • Genes encoding benzoyl-CoA reductase, a novel enzyme able to overcome the resonance stability of the aromatic ring, were identified by directed mutagenesis [8].
  • Enzyme activity analysis of proteins produced in vitro indicates that the GCHS2 reaction is a non-SS variant of the CHS reaction, with both different substrate specificity (to benzoyl-CoA) and a truncated catalytic profile [9].
  • Acetylene stimulated the benzoyl-CoA-independent ATPase activity and induced novel EPR signals with g(av) >2 [10].

Chemical compound and disease context of benzoyl-coenzyme A


Biological context of benzoyl-coenzyme A


Anatomical context of benzoyl-coenzyme A


Associations of benzoyl-coenzyme A with other chemical compounds


Gene context of benzoyl-coenzyme A

  • The Km values of human ACGNAT for benzoyl CoA, salicyl CoA, isovaleryl CoA and octanoyl CoA were 57.9, 83.7, 124 and 198 mM, respectively, and the corresponding Vmax values were 17.1, 10.1, 7.64 and 3.3 mumol/min/mg protein [26].
  • Benzoyl-CoA could also serve efficiently as an acyl donor for these hydroxylated alkaloids [27].
  • Purified benzoyl-CoA reductase preparations contained 0.25-0.3 mol FAD/mol enzyme [28].
  • Identification and characterization of the natural electron donor ferredoxin and of FAD as a possible prosthetic group of benzoyl-CoA reductase (dearomatizing), a key enzyme of anaerobic aromatic metabolism [28].
  • The two-electron reduction of benzoyl-CoA to a cyclic diene requires the cleavage of two molecules of ATP to ADP and P1 and is catalysed by benzoyl-CoA reductase [29].

Analytical, diagnostic and therapeutic context of benzoyl-coenzyme A


  1. Mechanism of ATP-driven electron transfer catalyzed by the benzene ring-reducing enzyme benzoyl-CoA reductase. Unciuleac, M., Boll, M. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  2. The final acylation step in taxol biosynthesis: cloning of the taxoid C13-side-chain N-benzoyltransferase from Taxus. Walker, K., Long, R., Croteau, R. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  3. BzdR, a repressor that controls the anaerobic catabolism of benzoate in Azoarcus sp. CIB, is the first member of a new subfamily of transcriptional regulators. Barragán, M.J., Blázquez, B., Zamarro, M.T., Mancheño, J.M., García, J.L., Díaz, E., Carmona, M. J. Biol. Chem. (2005) [Pubmed]
  4. Aerobic benzoyl-CoA catabolic pathway in Azoarcus evansii: studies on the non-oxygenolytic ring cleavage enzyme. Gescher, J., Eisenreich, W., Wörth, J., Bacher, A., Fuchs, G. Mol. Microbiol. (2005) [Pubmed]
  5. Iron-reducing bacteria unravel novel strategies for the anaerobic catabolism of aromatic compounds. Carmona, M., Díaz, E. Mol. Microbiol. (2005) [Pubmed]
  6. Reduction of benzenoid synthesis in petunia flowers reveals multiple pathways to benzoic Acid and enhancement in auxin transport. Orlova, I., Marshall-Colón, A., Schnepp, J., Wood, B., Varbanova, M., Fridman, E., Blakeslee, J.J., Peer, W.A., Murphy, A.S., Rhodes, D., Pichersky, E., Dudareva, N. Plant Cell (2006) [Pubmed]
  7. Taxol biosynthesis: molecular cloning of a benzoyl-CoA:taxane 2alpha-O-benzoyltransferase cDNA from taxus and functional expression in Escherichia coli. Walker, K., Croteau, R. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  8. A cluster of bacterial genes for anaerobic benzene ring biodegradation. Egland, P.G., Pelletier, D.A., Dispensa, M., Gibson, J., Harwood, C.S. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  9. Duplication and functional divergence in the chalcone synthase gene family of Asteraceae: evolution with substrate change and catalytic simplification. Helariutta, Y., Kotilainen, M., Elomaa, P., Kalkkinen, N., Bremer, K., Teeri, T.H., Albert, V.A. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  10. EPR and Mössbauer studies of benzoyl-CoA reductase. Boll, M., Fuchs, G., Meier, C., Trautwein, A., Lowe, D.J. J. Biol. Chem. (2000) [Pubmed]
  11. Chain initiation on the soraphen-producing modular polyketide synthase from Sorangium cellulosum. Wilkinson, C.J., Frost, E.J., Staunton, J., Leadlay, P.F. Chem. Biol. (2001) [Pubmed]
  12. Substrate binding and reduction of benzoyl-CoA reductase: evidence for nucleotide-dependent conformational changes. Möbitz, H., Friedrich, T., Boll, M. Biochemistry (2004) [Pubmed]
  13. Cyclohexa-1,5-diene-1-carbonyl-coenzyme A (CoA) hydratases of Geobacter metallireducens and Syntrophus aciditrophicus: Evidence for a common benzoyl-CoA degradation pathway in facultative and strict anaerobes. Peters, F., Shinoda, Y., McInerney, M.J., Boll, M. J. Bacteriol. (2007) [Pubmed]
  14. Reductive dehydroxylation of 4-hydroxybenzoyl-CoA to benzoyl-CoA in a denitrifying, phenol-degrading Pseudomonas species. Glöckler, R., Tschech, A., Fuchs, G. FEBS Lett. (1989) [Pubmed]
  15. BadM Is a Transcriptional Repressor and One of Three Regulators That Control Benzoyl Coenzyme A Reductase Gene Expression in Rhodopseudomonas palustris. Peres, C.M., Harwood, C.S. J. Bacteriol. (2006) [Pubmed]
  16. Genetic diversity of benzoyl coenzyme A reductase genes detected in denitrifying isolates and estuarine sediment communities. Song, B., Ward, B.B. Appl. Environ. Microbiol. (2005) [Pubmed]
  17. BadR, a new MarR family member, regulates anaerobic benzoate degradation by Rhodopseudomonas palustris in concert with AadR, an Fnr family member. Egland, P.G., Harwood, C.S. J. Bacteriol. (1999) [Pubmed]
  18. Benzylamine metabolism at low O2 concentrations. Relative sensitivities of monoamine oxidase, aldehyde dehydrogenase and hippurate synthesis to hypoxia. Jones, D.P. Biochem. Pharmacol. (1984) [Pubmed]
  19. Lipoic acid impairs glycine conjugation of benzoic acid and renal excretion of benzoylglycine. Gregus, Z., Fekete, T., Halászi, E., Klaassen, C.D. Drug Metab. Dispos. (1996) [Pubmed]
  20. Effects of fibrates on the glycine conjugation of benzoic acid in rats. Gregus, Z., Fekete, T., Halászi, E., Gyurasics, A., Klaassen, C.D. Drug Metab. Dispos. (1998) [Pubmed]
  21. Benzoyl-CoA ligase activity in the liver and kidney cortex of weanling guinea pigs treated with various inducers: relationship with hippurate synthesis and carnitine levels. Ali, A., Qureshi, I.A. Developmental pharmacology and therapeutics. (1992) [Pubmed]
  22. Benzophenone synthase and chalcone synthase from Hypericum androsaemum cell cultures: cDNA cloning, functional expression, and site-directed mutagenesis of two polyketide synthases. Liu, B., Falkenstein-Paul, H., Schmidt, W., Beerhues, L. Plant J. (2003) [Pubmed]
  23. Evidence for electrophilic catalysis in the 4-chlorobenzoyl-CoA dehalogenase reaction: UV, Raman, and 13C-NMR spectral studies of dehalogenase complexes of benzoyl-CoA adducts. Taylor, K.L., Liu, R.Q., Liang, P.H., Price, J., Dunaway-Mariano, D., Tonge, P.J., Clarkson, J., Carey, P.R. Biochemistry (1995) [Pubmed]
  24. 4-hydroxybenzoyl coenzyme A reductase (dehydroxylating) is required for anaerobic degradation of 4-hydroxybenzoate by Rhodopseudomonas palustris and shares features with molybdenum-containing hydroxylases. Gibson, J., Dispensa, M., Harwood, C.S. J. Bacteriol. (1997) [Pubmed]
  25. Biphenyl synthase from yeast-extract-treated cell cultures of Sorbus aucuparia. Liu, B., Beuerle, T., Klundt, T., Beerhues, L. Planta (2004) [Pubmed]
  26. Purification to homogeneity of mitochondrial acyl coa:glycine n-acyltransferase from human liver. Mawal, Y.R., Qureshi, I.A. Biochem. Biophys. Res. Commun. (1994) [Pubmed]
  27. Molecular characterization of a novel quinolizidine alkaloid O-tigloyltransferase: cDNA cloning, catalytic activity of recombinant protein and expression analysis in Lupinus plants. Okada, T., Hirai, M.Y., Suzuki, H., Yamazaki, M., Saito, K. Plant Cell Physiol. (2005) [Pubmed]
  28. Identification and characterization of the natural electron donor ferredoxin and of FAD as a possible prosthetic group of benzoyl-CoA reductase (dearomatizing), a key enzyme of anaerobic aromatic metabolism. Boll, M., Fuchs, G. Eur. J. Biochem. (1998) [Pubmed]
  29. Anaerobic metabolism of aromatic compounds. Heider, J., Fuchs, G. Eur. J. Biochem. (1997) [Pubmed]
  30. Two distinct pathways for anaerobic degradation of aromatic compounds in the denitrifying bacterium Thauera aromatica strain AR-1. Philipp, B., Schink, B. Arch. Microbiol. (2000) [Pubmed]
  31. SanJ, an ATP-dependent picolinate-CoA ligase, catalyzes the conversion of picolinate to picolinate-CoA during nikkomycin biosynthesis in Streptomyces ansochromogenes. Niu, G., Liu, G., Tian, Y., Tan, H. Metab. Eng. (2006) [Pubmed]
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