Efficient asymmetric hydrolysis of styrene oxide catalyzed by Mung bean epoxide hydrolases in ionic liquid-based biphasic systems

The asymmetric hydrolysis of styrene oxide to (R)-1-phenyl-1,2-ethanediol using Mung bean epoxide hydrolases was, for the first time, successfully conducted in an ionic liquid (IL)-containing biphasic system. Compared to aqueous monophasic system, IL-based biphasic systems could not only dissolve the substrate, but also effectively inhibit the non-enzymatic hydrolysis, and therefore markedly improve the reaction efficiency. Of all the tested ILs, the best results were observed in the biphasic system containing C4MIM·PF6, which exhibited good biocompatibility with the enzyme and was an excellent solvent for the substrate. 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 1/6, 35 °C, 6.5 and 100 mM, respectively, under which the initial reaction rate, the yield and the product e.e. were 18.4 mM/h, 49.4% and 97.0%. The biocatalytic process was shown to be feasible on a 500-mL preparative scale.

► Use of ILs to efficiently improve the biocatalytic hydrolysis of styrene oxide.
► Various ILs exerted significant but different effects on the reaction.
► The best performance of Mung bean epoxide hydrolase was observed with C4MIM·PF6.
► Substrate concentration (100 mM) and product e.e. (97%) were greatly improved.
► The efficient biocatalytic process was feasible on a 500-mL preparative scale.