Combined Imine Reductase and Amine Oxidase Catalyzed Deracemization of Nitrogen Heterocycles. Issue 1 (16th October 2015)

• Record Type: Journal Article
• Authors: Heath, Rachel S.; Pontini, Marta; Hussain, Shahed; Turner, Nicholas J.
• Is Part Of: ChemCatChem. Volume 8:Issue 1(2016)
• Page Start: 117
• Page End: 120
• Publication Date: 2015-10-16
• Subjects: amines -- deracemization -- enantioselectivity -- enzyme catalysis -- nitrogen heterocycles; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201500822
• Languages: English
• ISSNs: 1867-3880

Abstract

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. Abstract : N‐othing like it : A novel amine oxidase (AO)/imine reductase (IRED) system is 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 are deracemized to yield the ( S )‐amines in high yields and enantiomeric excess values. Other N‐heterocycles are deracemized with the aid of an AO in combination with ammonia borane.