Asymmetric Epoxidation of Long Chain Terminal Olefins byCorynebacterium equi, IFO 3730

Abstract
Among several type cultures that assimilated 1-hexadecene, C. equi IFO 3730 best accumulated 1,2-epoxyhexadecane. The purified product exhibited .**GRAPHIC**. 9.64 (c = 3.71, n-hexane) and had the (R) absolute configuration by correlating to known analogous compounds. The optical purity was 100% by PMR measurement of 1-methoxy-2-hexadecanol, which was derived stereospecifically from the epoxide. The highest yield (41% based on consumed 1-hexadecene) was achieved when 2.0% of octane and 0.1% of Tween 80 were added to the medium containing 0.5% of the olefin. C. equi also assimilated terminal olefins other than 1-hexadecene and produced the corresponding epoxides from substrates which have C chains longer than 14.

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