Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
ISSN-L : 1345-8957
Biochemistry and Biotechnology
Highly Selective and Asymmetric Reductive Biotransformation of α-Ionone by Epicoccum purpurascens
Kazuya ShimizuToshirou OnoMitsuo Miyazawa
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2013 Volume 62 Issue 4 Pages 231-234

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Abstract

The biotransformation of terpenoid C13 norisoprenoid (±)-α-ionone (1) using the plant pathogenic fungus Epicoccum purpurascens as a biocatalyst was investigated for the production of useful novel organic compounds. There are no reported biotransformations using E. purpurascens. The biotransformation of compound 1 via reduction of the C-9 ketone position yielded α-ionol (2) as the major metabolic product. Reduction of the racemic α-ionone [(–)-(6S)- and (+)-(6R)-] resulted in the exclusive formation of the two enantiomers (–)-(6S,9R)- and (+)-(6R,9S)-α-ionol (2). Thus, the enzymatic reduction of α-ionone by E. purpurascens proceeds with high asymmetry.

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© 2013 by Japan Oil Chemists' Society
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