Biosynthesis of acaterin: coupling of C(5) unit with octanoate.
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.
Sekiyama
Y
Y
Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo 152-8551, Japan.
Fujimoto
Y
Y
Hasumi
K
K
Endo
A
A
D002210:Caprylates / Q000378:metabolism*; D002247:Carbon Isotopes; D003903:Deuterium; D005227:Fatty Acids / Q000378:metabolism; D005285:Fermentation; D005663:Furans / Q000378:metabolism*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011549:Pseudomonas / Q000378:metabolism*
D002210:Caprylates; D002247:Carbon Isotopes; D005227:Fatty Acids; D005663:Furans; C077326:acaterin; D003903:Deuterium; C031492:octanoic acid