Production of Optically Active Epoxides by Microbial Oxidation of Olefins

Some of the microorganisms which assimilate hydrocarbons produce optically active epoxides from corresponding olefins. Although the substrates epoxidized by most of these microorganisms are restricted to aliphatic olefins, one of the gaseous olefin assimilating microorganisms, N.corallina, has been found to have a very wide substrate specificity in the epoxidation of olefins. This microorganism produces optically active epoxides from 1-alkenes (C3-C18), 2-alkenes, halogenated alkenes, styrene, phenyl allyl ether and their analogues. The rates of epoxidation of these substrates have been promoted by reducing the inhibitory effect of produced epoxides. In the epoxidation of moderate chain length 1-alkenes, the yield of (R) -1, 2-epoxides exceeded 80%. The optical purity of these 1, 2-epoxyalkanes ranges from 80 to 90% e.e.. These 1, 2-epoxyalkanes are now utilized as the intermediates in the syntheses of ferroelectric liquid crystals.