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Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles
Author(s) -
Heath Rachel S.,
Pontini Marta,
Hussain Shahed,
Turner Nicholas J.
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201500822
Subject(s) - chemistry , imine , amine oxidase , amine gas treating , enantiomeric excess , biocatalysis , organic chemistry , catalysis , enantiomer , monoamine oxidase , combinatorial chemistry , enzyme , enantioselective synthesis , reaction mechanism
A novel amine oxidase (AO)/imine reductase (IRED) system was developed for the deracemization of racemic amines. By combining ( R )‐6‐hydroxy‐ d ‐nicotine oxidase (6‐HDNO) with an ( R )‐IRED, a panel of racemic 2‐substituted piperidines and pyrrolidines were deracemized to yield the ( S )‐amines in high yields and enantiomeric excess values. Other N‐heterocycles were deracemized with monoamine oxidase (MAO‐N) or 6‐HDNO in combination with ammonia borane, which allowed comparison of the two enzyme deracemization approaches with that involving a chemical reducing agent.