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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| Format: | Article |
| Language: | deu |
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Swiss Chemical Society
1989-11-01
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| Series: | CHIMIA |
| Online Access: | https://www.chimia.ch/chimia/article/view/9930 |
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| _version_ | 1850140363308662784 |
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| author | Thierry Haag Tuneer Arslan Dieter Seebach |
| author_facet | Thierry Haag Tuneer Arslan Dieter Seebach |
| author_sort | Thierry Haag |
| collection | DOAJ |
| description |
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.
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| format | Article |
| id | doaj-art-e2b9c43b0e22439da4e8ce8bab3c96e2 |
| institution | OA Journals |
| issn | 0009-4293 2673-2424 |
| language | deu |
| publishDate | 1989-11-01 |
| publisher | Swiss Chemical Society |
| record_format | Article |
| series | CHIMIA |
| spelling | doaj-art-e2b9c43b0e22439da4e8ce8bab3c96e22025-08-20T02:29:51ZdeuSwiss Chemical SocietyCHIMIA0009-42932673-24241989-11-01431110.2533/chimia.1989.351Preparative β-Ketoester Reductions and Ester Hydrolyses by Yeast, Using Free Cells in Organic MediaThierry Haag0Tuneer Arslan1Dieter Seebach2Laboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH-8092 ZürichLaboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH-8092 ZürichLaboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH-8092 Zürich 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. https://www.chimia.ch/chimia/article/view/9930 |
| spellingShingle | Thierry Haag Tuneer Arslan Dieter Seebach Preparative β-Ketoester Reductions and Ester Hydrolyses by Yeast, Using Free Cells in Organic Media CHIMIA |
| title | Preparative β-Ketoester Reductions and Ester Hydrolyses by Yeast, Using Free Cells in Organic Media |
| title_full | Preparative β-Ketoester Reductions and Ester Hydrolyses by Yeast, Using Free Cells in Organic Media |
| title_fullStr | Preparative β-Ketoester Reductions and Ester Hydrolyses by Yeast, Using Free Cells in Organic Media |
| title_full_unstemmed | Preparative β-Ketoester Reductions and Ester Hydrolyses by Yeast, Using Free Cells in Organic Media |
| title_short | Preparative β-Ketoester Reductions and Ester Hydrolyses by Yeast, Using Free Cells in Organic Media |
| title_sort | preparative β ketoester reductions and ester hydrolyses by yeast using free cells in organic media |
| url | https://www.chimia.ch/chimia/article/view/9930 |
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