title: Highly selective and asymmetric reductive biotransformation of α-ionone by Epicoccum purpurascens.
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.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Osaka, Japan.
authors.forename: Kazuya
authors.initials: K
authors.lastname: Shimizu
authors.forename: Toshirou
authors.initials: T
authors.lastname: Ono
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Miyazawa
mesh_terms: D001203:Ascomycota / Q000378:metabolism*; D001711:Biotransformation; D002849:Chromatography, Gas; D045792:Norisoprenoids / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013997:Time Factors
chemical_list: D045792:Norisoprenoids; C011879:alpha-ionone