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Efficient synthesis of (S)-epichlorohydrin in high yield by cascade biocatalysis with halohydrin dehalogenase and epoxide hydrolase mutants

Paper ID Volume ID Publish Year Pages File Format Full-Text
49648 46757 2015 3 PDF Available
Title
Efficient synthesis of (S)-epichlorohydrin in high yield by cascade biocatalysis with halohydrin dehalogenase and epoxide hydrolase mutants
Abstract

•HheC was engineered for the stereoselective conversion of prochiral 1,3-DCP.•The best mutant (P175S/W249P) showed increased ee of (S)-ECH from 5% to 95.3%.•An efficient two-enzyme cascade route for the production of (S)-ECH was developed.•(S)-ECH was obtained in high yield (up to 91.2%) with > 99% ee.

Enantioselective biotransformation of prochiral 1,3-DCP by halohydrin dehalogenases (HHDHs) is particularly attractive since 100% yield of chiral epichlorohydrin (ECH) may be obtained. HheC mutant (P175S/W249P) displayed greatly improved enantiomeric excess (ee) of (S)-ECH from 5% to 95.3% in the catalyzed dehalogenation of 1,3-DCP at pH 8.0. (S)-ECH was enantioselectively biotransformed from 40 mM 1,3-DCP with 92.3% ee and 93.2% yield at pH 10.0. To increase the ee of (S)-ECH, the catalysis was carried out using HheC mutant coupled with epoxide hydrolase mutant and the maximum yield and ee of (S)-ECH reached 91.2% and > 99%.

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Keywords
1,3-Dicholoro-2-propanol; (S)-epichlorohydrin; Saturation mutagenesis; Halohydrin dehalogenase; Epoxide hydrolase; Cascade reaction
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Efficient synthesis of (S)-epichlorohydrin in high yield by cascade biocatalysis with halohydrin dehalogenase and epoxide hydrolase mutants
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 72, 5 December 2015, Pages 147–149
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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