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

Chem Commun (Camb). 2020 Jul 21;56(57):7949-7952. doi: 10.1039/d0cc02976a. Epub 2020 Jun 12.

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.

MeSH terms

  • Azepines / chemistry
  • Azepines / metabolism*
  • Galactose Oxidase / metabolism*
  • Imines / metabolism*
  • Molecular Structure
  • Oxidoreductases / metabolism*
  • Piperidines / chemistry
  • Piperidines / metabolism*

Substances

  • Azepines
  • Imines
  • Piperidines
  • Oxidoreductases
  • Galactose Oxidase