Biotransformation of Oleic Acid to Optically Active<i>γ</i>-Dodecalactone

Abstract

We contemplated the formation of γ-dodecalactone through microbial conversion consisting of two steps, the first for oxidizing oleic acid into 10-hydroxystearic acid and the second for the formation of γ-dodecalactone from the hydroxy acid. Microorganisms were screened for production of 10-hydroxystearic acid from oleic acid. A bacterium which could produce the hydroxy acid with a transformation yield of 61.5% at a concentration of 5% oleic acid was isolated. The hydroxy acid was found to be biotransformed to γ-dodecalactone by baker’s yeast. The enantiomeric composition of the biosynthetic γ-dodecalactone was estimated to be the (R)-configuration and the optical purity of the lactone was estimated to be 87.6% e.e. The biotransformation yield from oleic acid to γ-dodecalactone was 22.5%.