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

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20mmol/L,缓冲液pH=6.5以及35oC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5.42mmol/(L·h),49.2%和...

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Published in催化学报 Vol. 32; no. 9; pp. 1557 - 1563
Main Author 陈文静 娄文勇 王晓婷 宗敏华
Format Journal Article
LanguageChinese
Published 华南理工大学生物科学与工程学院,广东 广州,510006%华南理工大学应用生物催化实验室,广东 广州,510640%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 2011
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ISSN0253-9837
1872-2067
DOI10.3724/SP.J.1088.2011.10606

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Summary: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20mmol/L,缓冲液pH=6.5以及35oC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5.42mmol/(L·h),49.2%和94.3%.
Bibliography: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,
ISSN:0253-9837
1872-2067
DOI:10.3724/SP.J.1088.2011.10606