Using Ionic Liquid in a Biphasic System to Improve Asymmetric Hydrolysis of Styrene Oxide Catalyzed by Cross-Linked Enzyme Aggregates (CLEAs) of Mung Bean Epoxide Hydrolases

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• 作者：Chun-Yang Yu ; Ping Wei ; Xiao-Feng Li ; Min-Hua Zong ; Wen-Yong Lou
• 刊名：Industrial & Engineering Chemistry Research
• 出版年：2014
• 出版时间：May 14, 2014
• 年：2014
• 卷：53
• 期：19
• 页码：7923-7930
• 全文大小：355K
• 年卷期：v.53,no.19(May 14, 2014)
• ISSN：1520-5045

文摘

The asymmetric hydrolysis of racemic styrene oxide (SO) to (R)-1-phenyl-1,2-ethanediol using cross-linked enzyme aggregates (CLEAs) of epoxide hydrolases (EHs) from mung bean (mbEHs) was successfully conducted using ionic liquids (ILs) as cosolvents in biphasic systems. Of all the tested ILs, the best results were observed in the biphasic system containing [C₄MIM][PF₆] with better biocompatibility to the CLEAs of mbEHs. In the [C₄MIM][PF₆]/buffer biphasic system, it was found that the optimal volume ratio of IL to buffer, reaction temperature, buffer pH, and substrate concentration were 1:5, 40 掳C, 7.5, and 120 mM, respectively. Under the optimized reaction conditions, the initial reaction rate, yield, product ee, and E value reached 3.35 mmol/min, 49%, 95.8%, and 151, respectively, which were much higher than the corresponding values reported previously. Furthermore, the CLEAs exhibited markedly enhanced operational stability in a [C₄MIM][PF₆]-based biphasic system as compared with an n-hexane-based biphasic system. Additionally, the CLEAs of mbEHs-catalyzed process with the IL [C₄MIM][PF₆] was shown to be feasible on a 500 mL preparative scale, demonstrating their great potential for biosynthesis of chiral ortho-diols.