Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles

Rachel S. Heath; Marta Pontini; Shahed Hussain; Nicholas J. Turner

doi:10.1002/cctc.201500822

Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles

Rachel S. Heath, Marta Pontini, Shahed Hussain, Nicholas J. Turner^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	117-120
Number of pages	4
Journal	ChemCatChem
Volume	8
Issue number	1
Early online date	16 Oct 2015
DOIs	https://doi.org/10.1002/cctc.201500822
Publication status	Published - 7 Jan 2016

Keywords

amines
deracemization
enantioselectivity
enzyme catalysis
nitrogen heterocycles

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10.1002/cctc.201500822

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abstract = "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.",

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AU - Heath, Rachel S.

AU - Pontini, Marta

AU - Hussain, Shahed

AU - Turner, Nicholas J.

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KW - amines

KW - deracemization

KW - enantioselectivity

KW - enzyme catalysis

KW - nitrogen heterocycles

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Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles

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