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Vol. 26 No. 9 (2014): Vol 26 Issue 9

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Asymmetric Bioreduction of Ethyl (S)-4-chloro-3-hydroxy Butanoate Using Dried Baker's Yeast in Aqueous/Ionic Liquid Biphasic System

https://doi.org/10.14233/ajchem.2014.15950
Zhongqin Tan
Department of Applied Chemistry, College of Food Science and Biotechnology Engineering, Zhejiang Gongshang University, Hangzhou 310035, P.R. China
Huan Du
Department of Applied Chemistry, College of Food Science and Biotechnology Engineering, Zhejiang Gongshang University, Hangzhou 310035, P.R. China
Xiaoxiang Han
Department of Applied Chemistry, College of Food Science and Biotechnology Engineering, Zhejiang Gongshang University, Hangzhou 310035, P.R. China
Zheyao Yang
Department of Applied Chemistry, College of Food Science and Biotechnology Engineering, Zhejiang Gongshang University, Hangzhou 310035, P.R. China
Xiaodan Wu
Department of Applied Chemistry, College of Food Science and Biotechnology Engineering, Zhejiang Gongshang University, Hangzhou 310035, P.R. China

Corresponding Author(s) : Xiaoxiang Han

hxx74@126.com; han-xx74@163.com

Asian Journal of Chemistry, Vol. 26 No. 9 (2014): Vol 26 Issue 9

Abstract

A process of highly stereoselective reduction of ethyl 4-chloro-3-oxobutanoate to ethyl (S)-4-chloro-3-hydroxy butanoate with Baker's yeast was established. Compared with the aqueous/organic solvent biphasic system, the aqueous/ionic liquid biphasic system could eliminate high toxicity of organic solvent and make the convenience of product separation. Baker's yeast showed the best catalytic activity and enantioselectivity in the aqueous/[Bmim]PF6 biphasic system among the biphasic systems. Under the optimum conditions: [Bmim]PF6 180 g/L, dried baker's yeast 60 g/L, glucose 0.8 mol/L, ethyl 4-chloro-3-oxobutanoate 0.08 mol/L, temperature 30 °C, pH 7.0, 24 h and shaking speed 180 rpm, the yield and the e.e. value of (S)-4-chloro-3-hydroxy butanoate reached 92.6 % and 95.4 %, respectively.

Keywords

Ethyl 4-chloro-3-hydroxybutanoate Aqueous-ionic liquid biphasic system Baker's yeast
Tan, Z., Du, H., Han, X., Yang, Z., & Wu, X. (2014). Asymmetric Bioreduction of Ethyl (S)-4-chloro-3-hydroxy Butanoate Using Dried Baker’s Yeast in Aqueous/Ionic Liquid Biphasic System. Asian Journal of Chemistry, 26(9), 2695–2698. https://doi.org/10.14233/ajchem.2014.15950
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