MetaCyc Pathway: benzoyl-CoA biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: benzoyl-CoA biosynthesis

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: BiosynthesisAromatic 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

Expected Taxonomic Range: Bacteria , Embryophyta

General Background

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, Lu09]. Meanwhile, polyketides derived from benzoyl-CoA in bacteria may have antibiotic and other effects [Moore02a].

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 [Moore02a], 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 [Jarvis00].

Superpathways: hyperxanthone E biosynthesis

Unification Links: PlantCyc:PWY-6458

Created 10-Mar-2010 by Dreher KA, TAIR


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

Dudareva04: Dudareva N, Pichersky E, Gershenzon J (2004). "Biochemistry of plant volatiles." Plant Physiol 135(4);1893-902. PMID: 15326281

Jarvis00: 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

Lu09: Lu H (2009). "Dissection of salicylic acid-mediated defense signaling networks." Plant Signal Behav 4(8);713-7. PMID: 19820324

Moore02a: 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

Vlot09: Vlot AC, Dempsey DA, Klessig DF (2009). "Salicylic Acid, a multifaceted hormone to combat disease." Annu Rev Phytopathol 47;177-206. PMID: 19400653

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

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Abd02: Abd El-Mawla AM, Beerhues L (2002). "Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum." Planta 214(5);727-33. PMID: 11882941

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

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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

Van09: 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

Xiang02: Xiang L, Kalaitzis JA, Nilsen G, Chen L, Moore BS (2002). "Mutational analysis of the enterocin favorskii biosynthetic rearrangement." Org Lett 4(6);957-60. PMID: 11893195

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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