Journal
CHEMCATCHEM
Volume 8, Issue 1, Pages 117-120Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cctc.201500822
Keywords
amines; deracemization; enantioselectivity; enzyme catalysis; nitrogen heterocycles
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Funding
- European Union [266025]
- Marie Curie Initial Training Network (BIOTRAINS) [FP7-ITN-238531]
- Royal Society
- Biotechnology and Biological Sciences Research Council [BB/M006611/1] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [1273953] Funding Source: researchfish
- BBSRC [BB/M006611/1] Funding Source: UKRI
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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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