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《Chinese Journal of Catalysis》 2004-06
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Asymmetric Reduction of Ethyl 4-Chloro-3-Oxobutanoate to Ethyl 4-Chloro-3-Hydroxybutanoate by Yeast Cells in Aqueous Phase

YANG Zhonghua, YAO Shanjing * (Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China)  
The asymmetric reduction of ethyl 4-chloro-3-oxobutanoate (COBE) to optically active ethyl 4-chloro-3-hydroxybutanoate (CHBE) catalyzed by yeast cells in aqueous phase was investigated. The reduction was conducted in Tris-HCl buffer, and the concentrations of COBE and CHBE and the optical purity of product were determined by capillary GC and HPLC equipped with a chiralcel OB column, respectively. The product was mainly D-(S)-CHBE. Both the yield and the stereo-selectivity of CHBE were higher for the reaction. However, the product was mainly R-CHBE when the initial concentration of COBE was low, and the product was mainly S-CHBE when the initial concentration of COBE was higher. The CHBE had a few of inhibition effects on the reaction. In the COBE reduction, a co-substrate was required to regenerate the NAD(P)H. Ethanol, isopropanol and secondary butyl alcohol as the co-substrate were advantageous to the stereo-selectivity of S-CHBE, but glucose as the co-substrate could achieve higher yield. The higher temperature and pH 8 0 were favorable to the production of S-CHBE. The cells in logarithmic growth phase and cultured under anaerobic condition were also favorable to the stereo-selectivity of S-CHBE. 92% for yield and 90% for ee of S-CHBE were obtained respectively under appropriate reaction conditions.
【Fund】: 国家自然科学基金资助项目 ( 2 0 2 760 65 )
【CateGory Index】: O643
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【Co-citations】
Chinese Journal Full-text Database 7 Hits
1 YANG Zhonghua, YAO Shanjing * (Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China);An Effective Method for Controlling the Stereoselectivity in Asymmetric Reduction of β-Oxo Ester with Yeast Cells[J];Chinese Journal of Catalysis;2004-10
2 YU Ming'an 1* , ZHU Xiaobing2, QI Wei2, ZHAO Ling1, WEI Yumeng1(1 Department of Biomedical Engineering, Chongqing University of Medical Sciences, Chongqing 400016, China;2 Chongqing Daxin Pharmaceutical Company Limited, Chongqing 400700, China);Biocatalytic Synthesis of Ethyl (S)-(+)-3-Hydroxybutanoate by CTAB-Permeabilized Baker's Yeast Cells[J];Chinese Journal of Catalysis;2005-07
3 LIU Xiang 1,2, FANG Zhijie 1*, XU Jianhe3(1 School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, Jiangsu, China; 2 School of Chemical and Material Engineering, Southern Yangtze University, Wuxi 214036, Jiangsu, China; 3 State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China);Asymmetric Reduction of Aromatic Ketones with Yeast Cells[J];Chinese Journal of Catalysis;2006-01
4 ZHOU Ying,HE Junyao,WANG Pu,OU Zhimin,ZHOU Limin,ZU Lei(Institute of Biopharmaceutical Engineering,Zhejiang University of Technology,Hangzhou 310032,China);Progress in Studies of Preparation of Optically Active Ethyl-3-hydroxybutyrate by Microbial Whole-cells as Biocatalyst[J];Bulletin of Science and Technology;2008-01
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6 HUANG He,YANG Zhong-hua, YAO Shan-jing (Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027, China);Asymmetric reduction carbonyl compounds to chiral alcohols by baker's yeast[J];Chinese Journal of Bioprocess Engineering;2004-02
7 LI Yong-ning,SHI Xian-ai,MENG Chun,DONG Ya-qin,GUO Yang-hao(School of Biological Science and Technology,Fuzhou University,Fuzhou 350002,China);Asymmetric Synthesis of(S)-2-Octanol by Immobilized Yeast in Organic Solvent System[J];Pharmaceutical Biotechnology;2006-06
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1 LUO Xuan WANG Yong Ze WANG Jin Hua~* School of Biological Engineering,Hubei University of Technology,Hubei Wuhan 430068;A study on the Techniques for Asymmetry Reduction of Ketopantolactone by Bakers Yeast[A];[C];2007
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Chinese Journal Full-text Database 10 Hits
1 WANG Yun-ying1,2,XU Du-xin2 (1.School of Chemical Technology, Hefei University of Technolog y,Hefei230009,China; 2.School of Chemical and Material of Science,The University of Science and Technology of China,Hefei230036,China);Recent advanced in the chiral synthesis with biocatalyst[J];Journal of Anhui University(Natural Sciences);2003-03
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4 YU Ming'an 1* , ZHU Xiaobing2, QI Wei2, ZHAO Ling1, WEI Yumeng1(1 Department of Biomedical Engineering, Chongqing University of Medical Sciences, Chongqing 400016, China;2 Chongqing Daxin Pharmaceutical Company Limited, Chongqing 400700, China);Biocatalytic Synthesis of Ethyl (S)-(+)-3-Hydroxybutanoate by CTAB-Permeabilized Baker's Yeast Cells[J];Chinese Journal of Catalysis;2005-07
5 YANG Zhonghua~(1,2),YAO Shanjing~(1*),ZHAO Jun~1(1 Department of Chemical and Biochemical Engineering,Zhejiang University,Hangzhou 310027,Zhejiang,China;2 College of Chemical Engineering,Resources and Environment,Wuhan University of Science and Technology,Wuhan 430081,Hubei,China);Asymmetric Reduction of Acetophenone Catalyzed by Yeast Cells and Promotion Effect of Resin Adsorption on the Reaction[J];Chinese Journal of Catalysis;2005-10
6 JING Keju,XU Zhinan~*,LIN Jianping,CEN Peilin(Department of Chemical and Biochemical Engineering,Zhejiang University,Hangzhou 310027,Zhejiang,China);Asymmetric Reduction of Ethyl 4-Chloroacetoacetate to Ethyl (R)-(+)-4-Chloro-3-Hydroxybutyrate by Recombinant Escherichia coli[J];Chinese Journal of Catalysis;2005-11
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