期刊
CHEMCATCHEM
卷 10, 期 3, 页码 510-514出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201701408
关键词
amines; biocatalysis; chirality; imine reductase; reductive amination
资金
- CASE award from the UK Biotechnology and Biological Sciences Research Council (BBSRC)
- Pfizer [BB/L502406/1]
- BBSRC [BB/M006832/1]
- CASE studentship from Johnson Matthey
- ERC
- Biotechnology and Biological Sciences Research Council [BB/M006832/1] Funding Source: researchfish
- BBSRC [BB/M006611/1] Funding Source: UKRI
Reductive amination of carbonyl compounds constitutes one of the most efficient ways to rapidly construct chiral and achiral amine frameworks. Imine reductase (IRED) biocatalysts represent a versatile family of enzymes for amine synthesis through NADPH-mediated imine reduction. The reductive aminases (RedAms) are a subfamily of IREDs that were recently shown to catalyze imine formation as well as imine reduction. Herein, a diverse library of novel enzymes were expressed and screened as cell-free lysates for their ability to facilitate reductive amination to expand the known suite of biocatalysts for this transformation and to identify more enzymes with potential industrial applications. A range of ketones and amines were examined, and enzymes were identified that were capable of accepting benzylamine, pyrrolidine, ammonia, and aniline. Amine equivalents as low as 2.5 were employed to afford up to >99% conversion, and for chiral products, up to >98%ee could be achieved. Preparative-scale reactions were conducted with low amine equivalents (1.5 or 2.0) of methylamine, allylamine, and pyrrolidine, achieving up to >99% conversion and 76% yield.
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