title: Use of hydrophilic ionic liquids in a two-phase system to improve Mung bean epoxide hydrolases-mediated asymmetric hydrolysis of styrene oxide.
abstract: A comparative study was made of Mung bean epoxide hydrolases-catalyzed asymmetric hydrolysis of styrene oxide to (R)-1-phenyl-1,2-ethanediol in an n-hexane/buffer biphasic system containing various hydrophilic ionic liquids (ILs). Compared to the n-hexane/buffer biphasic system alone, addition of a small amount of hydrophilic ILs reduced the amount of non-enzymatic hydrolysis, and improved the reaction rate by up to 22%. The ILs with cation containing an alkanol group, namely [C(2)OHMIM][BF(4)] and [C(2)OHMIM][TfO], and the choline amino acid ILs [Ch][Arg] and [Ch][Pro] were found to be the most suitable co-solvents for the reaction, owing to their good biocompatibility with the enzyme, which led to high initial rates (0.99-1.25 μmol/min) and high product e.e.s (95%). When substrate concentration was around 30 mM, where optimal performance was observed with the IL-containing systems, the product e.e. was improved from 90% without ILs to ≥95% in the presence of ILs.
authors.affiliation: State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou 510006, Guangdong, China.
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Chen
authors.forename: Wen-Yong
authors.initials: WY
authors.lastname: Lou
authors.forename: Chun-Yang
authors.initials: CY
authors.lastname: Yu
authors.forename: Hong
authors.initials: H
authors.lastname: Wu
authors.forename: Min-Hua
authors.initials: MH
authors.lastname: Zong
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Smith
mesh_terms: D001709:Biotechnology; D004851:Epoxide Hydrolases / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D004852:Epoxy Compounds / Q000737:chemistry* / Q000378:metabolism; D007887:Fabaceae / Q000737:chemistry / Q000201:enzymology*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis / Q000187:drug effects; D057927:Hydrophobic and Hydrophilic Interactions; D007093:Imidazoles / Q000737:chemistry / Q000494:pharmacology; D052578:Ionic Liquids / Q000737:chemistry* / Q000494:pharmacology; D013696:Temperature
chemical_list: D004852:Epoxy Compounds; D007093:Imidazoles; D052578:Ionic Liquids; C013690:styrene oxide; D004851:Epoxide Hydrolases