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Stereoselective ring-opening of styrene oxide at elevated concentration by Phaseolus vulgaris epoxide hydrolase, PvEH2, in the organic/aqueous biphasic system
Catalysis Communications ( IF 3.7 ) Pub Date : 2019-01-31 , DOI: 10.1016/j.catcom.2019.01.024
Chuang Li , Bo-Chun Hu , Die Hu , Xiong-Feng Xu , Xun-Cheng Zong , Jin-Ping Li , Min-Chen Wu

To elevate the concentration of racemic styrene oxide (rac-SO), its asymmetric hydrolysis in organic/aqueous biphasic system was researched. Firstly, n-octane/phosphate buffer reaction system was constructed, where PvEH2 retained 75.9% activity at 25 °C for 8 h. Secondly, the optimal volume ratio of two phases and weight ratio of rac-SO to E. coli/pveh2 were 4:6 and 0.8. Then, the maximum allowable rac-SO concentration was assayed as 200 mM, 10-fold that in aqueous phase. Finally, the hydrolysis of rac-SO was performed, affording (R)-SO with over 99.5% ees and 47.8% yield, and (R)-phenyl-1,2-ethanediol with 93.6% eep and 50.4% yield in 12 h.



中文翻译:

在有机/水两相系统中,菜豆环氧化物水解酶Pv EH2升高浓度使苯乙烯氧化的立体选择性开环

为了提高外消旋苯乙烯氧化物(rac -SO)的浓度,研究了其在有机/水两相体系中的不对称水解。首先,构建了辛烷/磷酸盐缓冲液反应系统,其中Pv EH2在25°C下保持85.9%的活性。其次,两相的最佳体积比和rac -SO与大肠杆菌/ pveh2的重量比分别为4:6和0.8。然后,测定最大允许rac -SO浓度为200 mM,是水相的10倍。最后,进行rac -SO的水解,得到(R)-SO具有超过99.5%ee s产率为47.8%,(R)-苯基-1,2-乙二醇在12小时内的ee p为93.6%,产率为50.4%。

更新日期:2019-01-31
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