C. Hertweck, A. Jarvis, L. Xiang
Oct 1, 2001
Citations
1
Influential Citations
52
Citations
Journal
ChemBioChem
Abstract
The aromatic metabolite benzoic acid (1) is a biosynthetic building block of numerous benzoyl and benzyl groups that serve as important structural elements in a large number of natural products. In eukaryotes, for example, benzoate is a component of the zaragozic acids (2), paclitaxel (taxol ; 3), salicylic acid (4), and cocaine (5) (Figure 1). Although rarer in prokaryotic organisms, benzoyl-coenzyme A (benzoyl-CoA) is a starter unit for a few bacterial polyketides, such as enterocin (6) and the wailupemycins. Despite its simple structure and widespread occurrence, the biosynthesis of 1 and its thioester 1-CoA are only partially understood. In the field of plant secondary metabolism, two major routes from L-phenylalanine (7) to benzoic acid have been reported: the b-oxidation-type pathway (Scheme 1, route a) ; and the so-called nonoxidative pathway, via benzaldehyde (11) (Scheme 1, route b). 6, 7] Both routes possess common intermediates like cinnamoyl-CoA (8) and 3-hydroxy-3-phenylpropionyl-CoA (9-CoA) before branching to involve either oxidation and thiolation (route a) or retro-aldol cleavage followed by oxidation (route b). Until recently, the only known pathway from 7 to 1 in bacteria proceeded through two oxidative decarboxylation reactions involving the intermediates phenylpyruvate and phenylglyoxylate. We recently reported that the biosynthesis of 1 in the terrestrial plants Nicotiana attenuata and Cucumis sativus, and the marine actinomycete aStreptomyces maritimuso proceeds by a similar pathway involving the intermediate 3-hydroxy-3-phenylpropionate. Figure 1. Structures of some important natural products containing benzoatederived residues.