Combined microbial oxidation and reduction: a new approach to the highyield synthesis of homochiral unsaturated secondary alcohols from racemates
✍ Scribed by Giancarlo Fantin; Marco Fogagnolo; Pier Paolo Giovannini; Alessandro Medici; Paola Pedrini
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 355 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0957-4166
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✦ Synopsis
The oxidation of racemic secondary alcohols with Bacillus stearothermophilus followed by reduction of the mixture with Yarrowialipolytica to afford high yields of the enantiomerically pure R-alcohols la,b,d is described. Comparisons with Yarrowia lipolytica reduction, Bacillus stearothermophilus oxidation, and the contemporary use of the two microrganisms have been made.
Enantiomerically pure secondary alcohols are very common as pheromones, 1 aroma, flavour enhancing compounds, intermediates and chiral auxiliaries in organic synthesis. 2 The methodologies to obtain these chiral compounds are the microbial or enzymatic reduction of the corresponding ketones and the kinetic resolution of the racemic alcohols via esterification or hydrolysis of the corresponding esters with iipases. A broad range of ketones are reduced with Baker's yeast 3 or using purified alcohol dehydrogenases. 4 During the course of the