Biosynthetic studies of ω-cycloheptyl fatty acids in Alicyclobacillus cycloheptanicus. Formation of cycloheptanecarboxylic acid from phenylacetic acid

…, K Walker, I Tornus, S Handa, K Poralla…

Index: Moore, Bradley S.; Walker, Kevin; Tornus, Ingo; Handa, Sandeep; Poralla, Karl; Floss, Heinz G. Journal of Organic Chemistry, 1997 , vol. 62, # 7 p. 2173 - 2185

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Citation Number: 24

Abstract

The formation of the structurally novel, mono-substituted cycloheptane ring in ω-cycloheptyl fatty acids in Alicyclobacillus cycloheptanicus (formerly Bacillus cycloheptanicus) has been examined. Feeding experiments with 13C-and 2H-labeled intermediates demonstrated that cycloheptanecarboxylic acid (3), probably as its CoA thioester, is the starter unit for ω- cycloheptyl fatty acid biosynthesis. Analysis of the resultant labeling pattern from a feeding ...