Kulig, Justyna and Simon, Robert C. and Rose, Christopher A. and Husain, Syed Masood and Haeckh, Matthias and Luedeke, Steffen and Zeitler, Kirsten and Kroutil, Wolfgang and Pohl, Martina and Rother, Doerte (2012) Stereoselective synthesis of bulky 1,2-diols with alcohol dehydrogenases. CATALYSIS SCIENCE & TECHNOLOGY, 2 (8). pp. 1580-1589. ISSN 2044-4753,
Full text not available from this repository. (Request a copy)Abstract
Although biotransformations implementing alcohol dehydrogenases (ADHs) are widespread, enzymes which catalyse the reduction and oxidation of sterically demanding substrates, especially 2-hydroxy ketones, are still rare. To fill this gap eight ADHs were investigated concerning their potential to reduce bulky 2-hydroxy ketones. All of these enzymes showed good activities along with excellent enantio( ee > 99%) and diastereoselectivities (de > 99%). Due to their differences in substrate preferences and stereoselectivity a broad range of diastereomerically pure 1,2-diols is now accessible via biotransformation. Best results were obtained using the alcohol dehydrogenase from Ralstonia sp. (Cupriavidus sp.) (RADH), which showed a broad substrate range, especially for sterically demanding compounds. Araliphatic 2-hydroxy ketones, like (R)-2-hydroxy-1-phenylpropan-1-one ((R)-2-HPP), were reduced much faster than aliphatic or aromatic aldehydes (e. g. benzaldehyde) under the applied conditions. Additionally (R)-as well as (S)-2-hydroxy ketones were converted with high diastereoselectivities (de > 99%). RADH, which was up to now only studied as a whole cell biocatalyst overexpressed in E. coli, was purified and thoroughly characterised concerning its catalytic properties.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CATALYZED ENANTIOSELECTIVE DIBORATION; C BOND FORMATION; BENZALDEHYDE LYASE; ASYMMETRIC DIHYDROXYLATION; ENZYMATIC CARBOLIGATION; ACYLOIN CONDENSATIONS; 2-HYDROXY KETONES; HYDROXY KETONES; SIMPLE ALKENES; REDUCTION; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Dr. Kirsten Zeitler |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 25 May 2020 05:19 |
| Last Modified: | 25 May 2020 05:19 |
| URI: | https://pred.uni-regensburg.de/id/eprint/19463 |
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