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Reduction of bicyclo[3.2.0] hept-2-en-6-one and 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one using dehydrogenase enzymes and the fungus mortierella ramanniana
Authors:Suzanne Butt  HGeoff Davies  Michael J Dawson  Gordon C Lawrence  Jeff Leaver  Stanley M Roberts  Michael K Turner  Basil J Wakefield  Wilfred F Wall  John A Winders
Institution:1. Department of Microbiological Chemistry, Glaxo Group Research, Greenford, Middlesex, UB6 OHE, U.K.;2. Department of Medicinal Chemistry, Glaxo Group Research, Greenford, Middlesex, UB6 OHE, U.K.;3. Biotechnology Department, Glaxo Group Research, Greenford, Middlesex, UB6 OHE, U.K.;4. Department of Chemistry and Applied Chemistry, University of Salford, Salford, M5 4WT, U.K.
Abstract:Bicyclo3.2.0]hept-2-en-6-one (1) was reduced with an alcohol dehydrogenase from Thermoanaerobium brockii and a whole cell system (M. ramanniana) with excellent substrate enantioselectivity: 7,7-dimethylbicyclo3.2.0]hept-2-en-6-one (2) was similarly reduced using the 3α,20β-hydroxysteroid dehydrogenase from Streptomyces hydrogenans while M. ramanniana furnished both 6S-alcohols (4a), (6b) with high optical purity.
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