The stereochemistry of desaturations of long-chain fatty acids in Chlorella vulgaris

Abstract

1. A study was made of the stereospecificity of hydrogen removal in the sequential desaturations performed by intact cells of Chlorella vulgaris in the biosynthesis of oleic acid, linoleic acid and α-linolenic acid. 2. By use of erythro- and threo-9,10−2H2-, −12,13−2H2- and −15,16−2H2-labelled precursors, it was demonstrated that the pair of hydrogen atoms removed from each of these positions had the cis relative configuration. 3. That the hydrogen atoms removed in oleic acid and linoleic acid formation were of the d absolute configuration was proved by use of d- and l-9−3H-and −12−3H-labelled precursors. 4. The presence of a substantial kinetic isotope effect of deuterium at both positions of the putative double bond was indicated, suggesting that the mechanism of desaturation involves simultaneous concerted removal of the pair of hydrogen atoms.