title: Efficient asymmetric hydrolysis of styrene oxide catalyzed by Mung bean epoxide hydrolases in ionic liquid-based biphasic systems.
abstract: 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 C(4)MIM·PF(6), which exhibited good biocompatibility with the enzyme and was an excellent solvent for the substrate. In the C(4)MIM·PF(6)/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.
authors.affiliation: School of Biosciences and Biotechnology, South China University of Technology, Guangzhou 510006, China.
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Chen
authors.forename: Wen-Yong
authors.initials: WY
authors.lastname: Lou
authors.forename: Min-Hua
authors.initials: MH
authors.lastname: Zong
mesh_terms: D055162:Biocatalysis / Q000187:drug effects*; D002021:Buffers; D004851:Epoxide Hydrolases / Q000378:metabolism*; D004852:Epoxy Compounds / Q000378:metabolism*; D007887:Fabaceae / Q000187:drug effects / Q000201:enzymology*; D006868:Hydrolysis / Q000187:drug effects; D052578:Ionic Liquids / Q000494:pharmacology*; D044367:Phase Transition / Q000187:drug effects*
chemical_list: D002021:Buffers; D004852:Epoxy Compounds; D052578:Ionic Liquids; C013690:styrene oxide; D004851:Epoxide Hydrolases