催化学报

催化学报 ›› 2011, Vol. 32 ›› Issue (9): 1557-1563.DOI: 10.3724/SP.J.1088.2011.10606

• 研究论文 • 上一篇    

有机溶剂/缓冲液双相体系中绿豆环氧化物水解酶催化环氧苯乙烯不对称水解反应

陈文静1, 娄文勇2,a, 王晓婷2, 宗敏华3,b   

  1. 1华南理工大学生物科学与工程学院, 广东广州 510006; 2华南理工大学应用生物催化实验室, 广东广州 510640; 3华南理工大学轻工与食品学院制浆造纸工程国家重点实验室, 广东广州 510640
  • 收稿日期:2011-06-02 修回日期:2011-07-31 出版日期:2011-09-09 发布日期:2015-01-24

Asymmetric Hydrolysis of Styrene Oxide Catalyzed by Mung Bean Epoxide Hydrolase in Organic Solvent/Buffer Biphasic System

CHEN Wenjing1, LOU Wenyong2,a, WANG Xiaoting2, ZONG Minhua3,b   

  1. 1School of Biosciences and Biotechnology, South China University of Technology, Guangzhou 510006, Guangdong, China; 2Laboratory of Applied Biocatalysis, South China University of Technology, Guangzhou 510640, Guangdong, China; 3State Key Laboratory of Pulp and Paper Engineering, College of Light Industry and Food Sciences, South China University of Technology, Guangzhou 510640, Guangdong, China
  • Received:2011-06-02 Revised:2011-07-31 Online:2011-09-09 Published:2015-01-24

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1063

被引次数

14

摘要： 研究了有机溶剂/缓冲液双相体系中绿豆环氧化物水解酶高立体选择性地催化外消旋环氧苯乙烯水解生成 (R)-苯基乙二醇反应. 结果表明, 与单水相反应体系相比, 有机溶剂/缓冲液双相反应体系不仅有效地抑制环氧苯乙烯的非酶水解反应, 而且明显提高底物的浓度, 产物的收率和 ee 值更高. 在所考察的不同有机溶剂中, 正己烷不仅能较好地溶解底物, 而且对酶的毒性较小, 从而导致反应的初速率较快, 产物的收率和 ee 值较高, 是最适宜有机相. 在两相体积比 (正己烷/缓冲液) 为 1:1, 底物浓度为 20 mmol/L, 缓冲液 pH = 6.5 以及 35 oC 的最适反应条件下, 反应的初速率、产物的收率和 ee 值分别为 5.42 mmol/(L•h), 49.2% 和 94.3%.

关键词: 绿豆环氧化物水解酶, 环氧苯乙烯, (R)-苯基乙二醇, 有机溶剂/缓冲液双相体系, 不对称水解

Abstract: The biocatalytic asymmetric hydrolysis of styrene oxide to (R)-1-phenyl-1,2-ethanediol catalyzed by Mung bean epoxide hydrolase in organic solvent/buffer biphasic systems was studied. In comparison with an aqueous monophasic system, the organic solvent/buffer biphasic system not only inhibited effectively the non-enzymatic hydrolysis of styrene oxide, but also markedly improved the substrate concentration, product yield, and product ee value. Among various organic solvents examined, the n-hexane was the most suitable organic phase for the reaction. In the n-hexane/buffer biphasic system, the initial reaction rate was clearly faster and the product yield and product ee value were much higher owing to the excellent solvent property of n-hexane for styrene oxide and relatively good biocompatibility with Mung bean epoxide hydrolase. Moreover, the optimal volume ratio of n-hexane to buffer, reaction temperature, buffer pH value, and substrate concentration for the enzymatic hydrolysis were found to be 1:1, 35 oC, 6.5, and 20 mmol/L, respectively, under which the initial reaction rate, the product yield, and the product ee value were 5.42 mmol/(L·h), 49.2%, and 94.3%, respectively.

Key words: Mung bean epoxide hydrolase, styrene oxide, (R)-1-phenyl-1,2-ethanediol, organic solvent/buffer biphasic system, asymmetric hydrolysis