Biosynthesis of ω-cyclohexyl fatty acids in Alicyclobacillus acidocaldarius: the stereochemistry of the initial 1,4-conjugate elimination

Abstract

The 1,4-conjugate elimination of H ₂ O from shikimic acid 3, the initial step in the biosynthesis of ω-cyclohexyl fatty acids by the bacterium Alicyclobacillus acidocaldarius, has been shown to occur with an overall anti stereochemistry via loss of the pro-6R hydrogen of 3.