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.