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Use of hydrophilic ionic liquids in a two-phase system to improve Mung bean epoxide hydrolases-mediated asymmetric hydrolysis of styrene oxide

Paper ID Volume ID Publish Year Pages File Format Full-Text
23631 43459 2012 8 PDF Available
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 [C2OHMIM][BF4] and [C2OHMIM][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.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Addition of a small amount of hydrophilic ILs improved Mung bean EHs-catalyzed hydrolysis of SO. ► ILs effectively reduced the amount of non-enzymatic hydrolysis of SO. ► Diverse ILs showed different biocompatibility to EHs and effects on the reaction. ► ILs substantially increased the thermostability of Mung bean EHs. ► ILs affected the partition coefficients of the substrate between the two phases.

Keywords
Mung bean epoxide hydrolases; Styrene oxide; (R)-1-phenyl-1,2-ethanediol; Ionic liquids; Asymmetric hydrolysis
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Use of hydrophilic ionic liquids in a two-phase system to improve Mung bean epoxide hydrolases-mediated asymmetric hydrolysis of styrene oxide
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Biotechnology - Volume 162, Issues 2–3, 31 December 2012, Pages 183–190
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us