One‐pot Chemoenzymatic Deracemisation of Secondary Alcohols Employing Variants of Galactose Oxidase and Transfer Hydrogenation



Turner, Nicholas John, Yuan, Bo, Debecker, Damien P, Wu, Xiaofeng ORCID: 0000-0001-5549-8836, Xiao, Jianliang ORCID: 0000-0003-2010-247X and Fei, Qiang
(2020) One‐pot Chemoenzymatic Deracemisation of Secondary Alcohols Employing Variants of Galactose Oxidase and Transfer Hydrogenation. ChemCatChem, 12 (24). pp. 6191-6195.

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Abstract

<jats:title>Abstract</jats:title><jats:p>Enantiomerically enriched chiral secondary alcohols serve as valuable building blocks for drug intermediates and fine chemicals. In this study the deracemisation of secondary alcohols to generate enantiomeric pure chiral alcohols has been achieved by combining enantio‐selective enzymatic oxidation of a secondary alcohol, by a variant of GOase (GOase M<jats:sub>3‐5</jats:sub>), with either non‐selective ketone reduction via transfer hydrogenation (TH) or enantio‐selective asymmetric transfer hydrogenation (ATH). Both the enzymatic oxidation system and the transition‐metal mediated reduction system were optimised to ensure compatibility with each other resulting in a homogeneous reaction system. 1‐(4‐nitrophenyl)ethanol was generated with 99 % conversion and 98 % <jats:italic>ee</jats:italic> by the deracemisation method, and it has been extended to a series of other secondary alcohols with comparable results.</jats:p>

Item Type: Article
Uncontrolled Keywords: biocatalysis, chiral secondary alcohols, galactose oxidase, deracemisation, transfer hydrogenation
Depositing User: Symplectic Admin
Date Deposited: 08 Oct 2020 10:17
Last Modified: 18 Sep 2023 19:05
DOI: 10.1002/cctc.202001191
Related URLs:
URI: https://livrepository.liverpool.ac.uk/id/eprint/3103871