Synthesis of protected 3-aminopiperidine and 3-aminoazepane derivatives using enzyme cascades.

Chemical Communications : Chem Comm
Grayson J FordSabine L Flitsch

Abstract

Multi-enzyme cascades utilising variants of galactose oxidase and imine reductase led to the successful conversion of N-Cbz-protected l-ornithinol and l-lysinol to l-3-N-Cbz-aminopiperidine and l-3-N-Cbz-aminoazepane respectively, in up to 54% isolated yield. Streamlining the reactions into one-pot prevented potential racemisation of key labile intermediates and led to products with high enantiopurity.

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Citations

Oct 9, 2020·Natural Product Reports·Robert A Hill, Andrew Sutherland
Sep 18, 2020·Chembiochem : a European Journal of Chemical Biology·Peter StockingerBettina M Nestl
Aug 28, 2021·Biotechnology Advances·Jing FengBian Wu
Jan 14, 2022·Chemical Communications : Chem Comm·Freya TadayElaine O'Reilly

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