Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Asymmetric Epoxidation of Long Chain Terminal Olefins by Corynebacterium equi IFO 3730
Hiromichi OHTAHatsuki TETSUKAWA
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1979 Volume 43 Issue 10 Pages 2099-2104

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Abstract
Among several type cultures that assimilated 1-hexadecene, Corynebacterium equi IFO 3730 was found to best accumulate 1, 2-epoxyhexadecane. The purified product exhibited [α]25D+9.64 (c=3.71, n-hexane) and was confirmed to have the (R) absolute configuration by correlating to known analogous compounds. The optical purity was determined to be 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 carbon chains longer than fourteen.
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