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Biological enantioselective reduction of methylcyclohexanones by Glomerella cingulata
Author(s) -
Miyazawa Mitsuo,
Okamura Shigeaki,
Kameoka Hiromu
Publication year - 1996
Publication title -
journal of chemical technology and biotechnology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.64
H-Index - 117
eISSN - 1097-4660
pISSN - 0268-2575
DOI - 10.1002/(sici)1097-4660(199602)65:2<171::aid-jctb396>3.0.co;2-6
Subject(s) - enantioselective synthesis , chemistry , glomerella cingulata , enantiomer , ketone , enantiomeric excess , stereospecificity , metabolite , optical rotation , stereochemistry , organic chemistry , botany , catalysis , biology , colletotrichum gloeosporioides , biochemistry
Biological reduction of alkylcyclohexanones by Glomerella cingulata was studied. With this organism regioisomeric 2‐, 3‐ or 4‐methylcyclohexanone gave the corresponding cis ‐ and trans ‐methylcyclohexanols. The major metabolites of (±)‐2‐ and (±)‐3‐methylcyclohexanone were cis ‐2‐ and cis ‐3‐methylcyclohexanol. On the other hand, 4‐methylcyclohexanone yielded mainly the trans ‐4‐methylcyclohexanol. In addition, the metabolites from (±)‐2‐ and (±)‐3‐methylcyclohexanone indicated enantioselective reduction by specific optical rotation of the products. The enantiomeric excesses of the microbiological reduction products were determined by NMR spectra of (+)‐MTPA‐esters of the alcohols produced. The reduction of (±)‐2‐methylcyclohexanone was stereospecific, with the (2 R )‐ketone being converted to the corresponding (+)‐ cis ‐2‐methylcyclohexanol (1 S ‐2 R ); absolute configuration, 92% e.e. On the other hand, the enantiomeric excess of the major metabolite of (±)‐3‐methylcyclohexanone was (−)‐ cis ‐3‐methylcyclohexanol (1 S ‐3 R ); absolute configuration, 33% e.e.