Abstract
The formation of the cyclohexanecarboxylic acid starter unit of ω-cyclohexyl fatty acids from shikimic acid in Alicyclobacillus acidocaldarius (formerly Bacillus acidocaldarius) has been studied. Feeding experiments with 13 C- and 2 H-labeled samples of shikimic acid and potential intermediates in the wild type and two blocked mutants demonstrated that the formation of cyclohexanecarboxylic acid in this organism follows the same pathway as in Streptomyces collinus (J. Am. Chem. Soc., preceding paper in this issue). (1S,3S)-3-Hydroxycyclohexanecarboxylic acid (20) is accumulated by blocked mutant 2, indicating that 5-hydroxycyclohex-1-enecarboxylic acid (6) is first reduced to the hydroxy acid 20 and then dehydrated to 2-cyclohexenecarboxylic acid (8)
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