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《Chinese Journal of Catalysis》 2005-10
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Asymmetric Reduction of Acetophenone Catalyzed by Yeast Cells and Promotion Effect of Resin Adsorption on the Reaction

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)  
Optically active aryl alcohols are the most important chiral building blocks for many single enantiomer pharmaceuticals.Asymmetric reduction of prochiral ketones to these chiral alcohols by active microbial cells is one of the most promising routes.The asymmetric reduction of acetophenone(ACP) to chiral α-phenylethyl alcohol(PEA) in an aqueous phase catalyzed by Saccharomyces cerevisiae cells was studied as a model reaction.ACP can be selectively reduced to(S)-PEA with excellent stereoselectivity.The enantiomeric excess of(S)PEA reaches as high as 99%.The appropriate conditions for this reaction are pH=7.0~8.0 and 0.2 g/ml of cells.(S)-PEA can be selectively oxidized to ACP by the yeast cells.The high concentration substrate has obvious toxicity to the cells and inhibits the reaction.In order to avoid the toxicity and increase the initial substrate concentration,the introduction of macroporous adsorption resins to the reaction system was investigated.The adsorption ability of the resin to ACP should not be too strong.The initial ACP concentration can be increased remarkably to 72.2 mmol/L when an appropriate resin was used.
【Fund】: 国家自然科学基金资助项目(20276065)
【CateGory Index】: O643.32
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【References】
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【Citations】
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1 YANG Zhonghua, YAO Shanjing * (Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China);Asymmetric Reduction of Ethyl 4-Chloro-3-Oxobutanoate to Ethyl 4-Chloro-3-Hydroxybutanoate by Yeast Cells in Aqueous Phase[J];Chinese Journal of Catalysis;2004-06
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【Co-citations】
Chinese Journal Full-text Database 10 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
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4 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
5 MA Xiaokui~(1*),WANG Zhezhi~1,CHEN Wuling~2(1 College of Life Sciences,Shaanxi Normal University,Xi′an 710062,Shaanxi,China;2 College of Life Sciences,Northwest University,Xi′an 710069,Shaanxi,China);Asymmetric Reduction of Ethyl 4-Chloro-3-Oxobutanoate to Ethyl 4-Chloro3-Hydroxybutanoate Directly Catalyzed by Yeast Fermentation Broth[J];Chinese Journal of Catalysis;2006-04
6 YING Xiaojiao, YAO Shanjing, GUAN Yixin(Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China);Asymmetric Reduction of Acetophenone to α-Phenylethanol by Candida valida under Compressed CO_2[J];Chinese Journal of Catalysis;2006-07
7 L Tengfei,XU Yan,MU Xiaoqing,NIE Yao(Key Laboratory of Industrial Biotechnology of the Ministry of Education,Southern Yangtze University,Wuxi 214036,Jiangsu,China);Promotion Effect of Xylose Co-substrate on Stability of Catalytic System for Asymmetric Redox of(R,S)-1-Phenyl-1,2-ethanediol to Its (S)-Enantiomer by Candida Parapsilosis[J];Chinese Journal of Catalysis;2007-05
8 HE Jun-yao, SUN Zhi-hao, ZHENG Pu, HAN Li (Laboratory of Biocatalysis, School of Biotechnology, Key Laboratory of Industrial Biotechnology, Ministry of Education, Southern Yangtze University, Wuxi 214036, China);Asymmetric Reduction of Ethyl 4-Chloro-3-Oxobutanoate in an Aqueous/Organic Solvent Biphasic System with Microorganism[J];Journal of Chemical Engineering of Chinese Universities;2007-02
9 RUAN Wen-bing,LIN Mei-xin,CHEN Su-hua,XU Xiao-ping (College of Chemistry and Chemical Engineering,Fuzhou University,Fuzhou,Fujian 350108,China);Determination of mandelic acid and phenylglyoxilic acid in chiral biotransformation by ion-pair reversed-phase high-performance liquid chromatography[J];Journal of Fuzhou University(Natural Science Edition);2010-02
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【Co-references】
Chinese Journal Full-text Database 10 Hits
1 ZHU Ping (Dept.Chem.& Chem.Engn.,Baoji Coll. Arts & Sci., Baoji 721007,Shaanxi,China);Chiral molecules research :past,present ,and future[J];Journal of Baoji College of Arts and Science(Natural Science Edition);2002-01
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3 LIU Senlin, ZONG Minhua *, TU Ran, ZHOU Fan (Department of Biotechnology, South China University of Technology, Guangzhou 510640, China);Asymmetric Synthesis of (R)-Mandelonitrile Catalysed by ( R )-Oxynitrilase from Almond in Water/Organic Solvent Biphase Systems[J];Chinese Journal of Catalysis;2001-01
4 YANG Zhonghua, YAO Shanjing * (Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China);Asymmetric Reduction of Ethyl 4-Chloro-3-Oxobutanoate to Ethyl 4-Chloro-3-Hydroxybutanoate by Yeast Cells in Aqueous Phase[J];Chinese Journal of Catalysis;2004-06
5 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
6 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
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9 MA Xiaokui~(1*),WANG Zhezhi~1,CHEN Wuling~2(1 College of Life Sciences,Shaanxi Normal University,Xi′an 710062,Shaanxi,China;2 College of Life Sciences,Northwest University,Xi′an 710069,Shaanxi,China);Asymmetric Reduction of Ethyl 4-Chloro-3-Oxobutanoate to Ethyl 4-Chloro3-Hydroxybutanoate Directly Catalyzed by Yeast Fermentation Broth[J];Chinese Journal of Catalysis;2006-04
10 YING Xiaojiao, YAO Shanjing, GUAN Yixin(Department of Chemical and Biochemical Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China);Asymmetric Reduction of Acetophenone to α-Phenylethanol by Candida valida under Compressed CO_2[J];Chinese Journal of Catalysis;2006-07
【Secondary References】
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4 GUO Jinling,MU Xiaoqing,XU Yan (Key Laboratory of Industrial Biotechnology of Ministry of Education,Jiangnan University,Wuxi 214122,Jiangsu,China);Asymmetric synthesis of (R)-methyl mandelate by yeast coupled with in situ product removal technique[J];Chemical Industry and Engineering Progress;2010-03
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