Highly Efficient Synthesis of Optically Pure (S)‐1‐phenyl‐1,2‐ethanediol by a Self‐Sufficient Whole Cell Biocatalyst

ChemistryOpen

Dr. Xi Chen¹  Ting Mei¹  Yunfeng Cui¹  Qijia Chen¹  Xiangtao Liu¹  Prof. Jinhui Feng¹  Prof. Qiaqing Wu¹ 

[1] National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences, Tianjin, P. R. China

关键词: asymmetric synthesis;    biocatalysis;    bioreductions;    carbonyl reductases;    stereochemistry;    vicinal diols;   

DOI  :  10.1002/open.201500045

来源: Wiley

【 摘 要 】

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.

【 授权许可】

CC BY-NC-ND   
© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

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