Preparative β-Ketoester Reductions and Ester Hydrolyses by Yeast, Using Free Cells in Organic Media

Free cells of yeast have been used for preparative β-ketoester reductions and ester hydrolyses in a mixture of isopropyl hexadecanoate and soybean phospholipids. The commercially available pressed lager baker’s yeast was used without adding water to the organic medium. In this way, ca. 50 g substra...

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Bibliographic Details
Main Authors: Thierry Haag, Tuneer Arslan, Dieter Seebach
Format: Article
Language:deu
Published: Swiss Chemical Society 1989-11-01
Series:CHIMIA
Online Access:https://www.chimia.ch/chimia/article/view/9930
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Summary:Free cells of yeast have been used for preparative β-ketoester reductions and ester hydrolyses in a mixture of isopropyl hexadecanoate and soybean phospholipids. The commercially available pressed lager baker’s yeast was used without adding water to the organic medium. In this way, ca. 50 g substrate could be easily converted by 500-700 g yeast in a 1.5 L volume, thus surpassing the reported procedures in aqueous media. Switching from aqueous to organic medium led, in a couple of cases, to an increase of the enantioselectivity from 90% (in water) to > 99% ee (in the organic medium) for ketone reduction and from 74 % to > 99 % ee for ester hydrolysis as compared to the best reported data for aqueous conditions.
ISSN:0009-4293
2673-2424