This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.
Synonyms: benzoyl-coenzyme A biosynthesis
|Superclasses:||Biosynthesis → Aromatic Compounds Biosynthesis|
Some taxa known to possess this pathway include : Arabidopsis thaliana col , Catharanthus roseus , Cucumis sativus , Hypericum androsaemum , Nicotiana tabacum , Petunia x hybrida , Streptomyces maritimus
Benzoyl-CoA is an important precursor to a number of different compounds. In plants, volatile benzenoids derived from benzoyl-CoA, such as benzylbenzoate, can serve as aroma compounds [DAuria02, Dudareva04, Boatright04] or defense signals [Vlot09, Lu09b]. Meanwhile, polyketides derived from benzoyl-CoA in bacteria may have antibiotic and other effects [Moore02b].
About This Pathway
Following the initial activation of trans-cinnamic acid with CoA in the trans-cinnamoyl-CoA biosynthesis pathway, the three reactions shown in this pathway are expected to share similarities with the β-oxidation process involved in fatty acid metabolism. These reactions, from (E)-cinnamoyl-CoA to benzoyl-CoA will likely require the sequential activities of an enoyl-CoA hydratase, a dehydrogenase, and a thiolase [Boatright04].
Enzymes catalyzing two of these steps have been identified in bacteria [Moore02b], but the dehydrogenase has not yet been found. In plants, none of the enzymes predicted to participate in this pathway have been cloned or characterized to date, but radiotracer studies provide strong evidence for the existence of this pathway [Jarvis00a].
Superpathways: hyperxanthone E biosynthesis
Unification Links: PlantCyc:PWY-6458
Boatright04: Boatright J, Negre F, Chen X, Kish CM, Wood B, Peel G, Orlova I, Gang D, Rhodes D, Dudareva N (2004). "Understanding in vivo benzenoid metabolism in petunia petal tissue." Plant Physiol 135(4);1993-2011. PMID: 15286288
DAuria02: D'Auria JC, Chen F, Pichersky E (2002). "Characterization of an acyltransferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri." Plant Physiol 130(1);466-76. PMID: 12226525
Jarvis00a: Jarvis AP, Schaaf O, Oldham NJ (2000). "3-hydroxy-3-phenylpropanoic acid is an intermediate in the biosynthesis of benzoic acid and salicylic acid but benzaldehyde is not." Planta 212(1);119-26. PMID: 11219576
Moore02b: Moore BS, Hertweck C, Hopke JN, Izumikawa M, Kalaitzis JA, Nilsen G, O'Hare T, Piel J, Shipley PR, Xiang L, Austin MB, Noel JP (2002). "Plant-like biosynthetic pathways in bacteria: from benzoic acid to chalcone." J Nat Prod 65(12);1956-62. PMID: 12502351
Xiang03: Xiang L, Moore BS (2003). "Characterization of benzoyl coenzyme A biosynthesis genes in the enterocin-producing bacterium "Streptomyces maritimus"." J Bacteriol 185(2);399-404. PMID: 12511484
Gasson98: Gasson MJ, Kitamura Y, McLauchlan WR, Narbad A, Parr AJ, Parsons EL, Payne J, Rhodes MJ, Walton NJ (1998). "Metabolism of ferulic acid to vanillin. A bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage of a hydroxycinnamic acid SCoA thioester." J Biol Chem 273(7);4163-70. PMID: 9461612
Hertweck01: Hertweck C, Jarvis AP, Xiang L, Moore BS, Oldham NJ (2001). "A mechanism of benzoic acid biosynthesis in plants and bacteria that mirrors fatty acid beta-oxidation." Chembiochem 2(10);784-6. PMID: 11948863
Narbad98: Narbad A, Gasson MJ (1998). "Metabolism of ferulic acid via vanillin using a novel CoA-dependent pathway in a newly-isolated strain of Pseudomonas fluorescens." Microbiology 144 ( Pt 5);1397-405. PMID: 9611814
Piel00: Piel J, Hertweck C, Shipley PR, Hunt DM, Newman MS, Moore BS (2000). "Cloning, sequencing and analysis of the enterocin biosynthesis gene cluster from the marine isolate 'Streptomyces maritimus': evidence for the derailment of an aromatic polyketide synthase." Chem Biol 7(12);943-55. PMID: 11137817
Rabus02: Rabus R, Kube M, Beck A, Widdel F, Reinhardt R (2002). "Genes involved in the anaerobic degradation of ethylbenzene in a denitrifying bacterium, strain EbN1." Arch Microbiol 178(6);506-16. PMID: 12420173
Rubio06: Rubio S, Larson TR, Gonzalez-Guzman M, Alejandro S, Graham IA, Serrano R, Rodriguez PL (2006). "An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment." Plant Physiol 140(3);830-43. PMID: 16415216
Van09a: Van Moerkercke A, Schauvinhold I, Pichersky E, Haring MA, Schuurink RC (2009). "A plant thiolase involved in benzoic acid biosynthesis and volatile benzenoid production." Plant J 60(2);292-302. PMID: 19659733
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