Author:
Cane David E.,Weiner Steven W.
Abstract
Pentalenene synthase catalyzes the cyclization of farnesyl diphosphate (1) to the sesquiterpene hydrocarbon pentalenene (4). Separate incubations of (4S,8S)-[4,8-3H2, 4,8-14C2]farnesyl diphosphate (1a) and (4R,8R)-[4,8-3H2, 4,814C2]farnesyl diphosphate (1b) with pentalenene synthase isolated from Streptomyces UC5319 and analysis of the derived labeled pentalenenes, 4a and 4b, respectively, by chemical degradation established that H-8si of FPP was lost upon cyclization to pentalenene. Consideration of the plausible conformations of the enzymatic cyclization intermediates indicates that the electrophilic allylic addition-elimination (SE′) reaction in which the C-4,5 bond of pentalenene is formed involves an orthogonal relationship between the C—C bond being formed and the C—H bond that is ultimately broken.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
31 articles.
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