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Stereoselective reduction of (±)‐bicyclo[3.3.1]nonane‐2,6‐dione by microorganisms
Author(s) -
Miyazawa Mitsuo,
Nobata Masahiro,
Okamura Shigeaki,
Muraoka Osamu,
Tanabe Genzoh,
Kameoka Hiromu
Publication year - 1998
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(199804)71:4<281::aid-jctb837>3.0.co;2-e
Subject(s) - nonane , bicyclic molecule , diol , glomerella cingulata , chemistry , diketone , stereochemistry , biotransformation , organic chemistry , biology , botany , colletotrichum gloeosporioides , enzyme
The biotransformation of (±)‐bicyclo[3.3.1]nonane‐2,6‐dione by Aspergillus niger and Glomerella cingulata was investigated. The diketone was reduced to the ketoalcohol 2‐ endo ‐hydroxy‐bicyclo[3.3.1]nonane‐6‐one and the diol endo , endo ‐bicyclo[3.3.1]nonane‐2,6‐diol respectively. Endo , endo ‐bicyclo[3.3.1]nonane‐2,6‐diol and ketoalcohols produced by G . cingulata had high optical purity, on the other hand, reduction by A . niger yielded optically active (‐)‐(1 R , 2 S , 5 R , 6 S )‐bicyclo[3.3.1]nonane‐2,6‐diol(99·9% e.e.). © 1998 SCI