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- Title
Highly Efficient Synthesis of Optically Pure ( S)-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst.
- Authors
Chen, Xi; Mei, Ting; Cui, Yunfeng; Chen, Qijia; Liu, Xiangtao; Feng, Jinhui; Wu, Qiaqing; Zhu, Dunming
- Abstract
Terminal vicinal diols are important chiral building blocks and intermediates in organic synthesis. Reduction of α-hydroxy ketones provides a straightforward approach to access these important compounds. In this study, it has been found that asymmetric reduction of a series of α-hydroxy aromatic ketones and 1-hydroxy-2-pentanone, catalyzed by Candida magnolia carbonyl reductase (CMCR) with glucose dehydrogenase (GDH) from Bacillus subtilis for cofactor regeneration, afforded 1-aryl-1,2-ethanediols and pentane-1,2-diol, respectively, in up to 99 % ee. In order to evaluate the efficiency of the bioreduction, lyophilized recombinant Escherichia coli whole cells coexpressing CMCR and GDH genes were used as the biocatalyst and α-hydroxy acetophenone as the model substrate, and the reaction conditions, such as pH, cosolvent, the amount of biocatalyst and the presences of a cofactor (i.e., NADP+), were optimized. Under the optimized conditions (pH 6, 16 h), the bioreduction proceeded smoothly at 1.0 m substrate concentration without the external addition of cofactor, and the product ( S)-1-phenyl-1,2-ethanediol was isolated with 90 % yield and 99 % ee. This offers a practical biocatalytic method for the preparation of these important vicinal diols.
- Subjects
ETHYLENE glycols; GLYCOL synthesis; GLYCOLS; DEHYDROGENASES; BACILLUS subtilis; ENZYMES
- Publication
ChemistryOpen, 2015, Vol 4, Issue 4, p483
- ISSN
2191-1363
- Publication type
Article
- DOI
10.1002/open.201500045