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Biosynthesis of acaterin: coupling of C(5) unit with octanoate
Y Sekiyama1, Y Fujimoto, K Hasumi
1Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo 152-8551, Japan.
The Journal of Organic Chemistry
|August 21, 2001
Abstract:
Acaterin (1), produced by Pseudomonas sp. A 92, is a secondary metabolite having a 2-penten-4-olide structure. Feeding experiments with (2)H- and (13)C-labeled decanoic acid, their 3-oxygenated congeners, and octanoic acid have suggested that 1 is biosynthesized via coupling of a C(5) unit with octanoate, rather than via introduction of a C(3) unit at the alpha position of a decanoate derivative. Further feeding study of [2,3-(13)C(2)]decanoic acid concluded that the former route is operating in the biosynthesis of 1.