title: Highly Efficient Synthesis of Optically Pure (S)-1-phenyl-1,2-ethanediol by a Self-Sufficient Whole Cell Biocatalyst.
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.
authors.affiliation: National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences Tianjin, 300308, P. R. China.
authors.forename: Xi
authors.initials: X
authors.lastname: Chen
authors.affiliation: National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences Tianjin, 300308, P. R. China ; College of Bioengineering, Tianjin University of Science and Technology Tianjin, 300457, P. R. China.
authors.forename: Ting
authors.initials: T
authors.lastname: Mei
authors.affiliation: National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences Tianjin, 300308, P. R. China.
authors.forename: Yunfeng
authors.initials: Y
authors.lastname: Cui
authors.affiliation: National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences Tianjin, 300308, P. R. China ; University of Chinese Academy of Sciences Beijing, 100049, P. R. China.
authors.forename: Qijia
authors.initials: Q
authors.lastname: Chen
authors.affiliation: National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences Tianjin, 300308, P. R. China.
authors.forename: Xiangtao
authors.initials: X
authors.lastname: Liu
authors.affiliation: National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences Tianjin, 300308, P. R. China.
authors.forename: Jinhui
authors.initials: J
authors.lastname: Feng
authors.affiliation: National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences Tianjin, 300308, P. R. China.
authors.forename: Qiaqing
authors.initials: Q
authors.lastname: Wu
authors.affiliation: National Engineering Laboratory for Industrial Enzymes and Tianjin Engineering Center for Biocatalytic Technology, Tianjin Institute of Industrial Biotechnology, Chinese Academy of Sciences Tianjin, 300308, P. R. China ; University of Chinese Academy of Sciences Beijing, 100049, P. R. China.
authors.forename: Dunming
authors.initials: D
authors.lastname: Zhu
keywords: asymmetric synthesis; biocatalysis; bioreductions; carbonyl reductases; stereochemistry; vicinal diols