Biocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades

Jeremy I. Ramsden, Rachel S. Heath, Sasha R. Derrington, Sarah L. Montgomery, Juan Mangas-Sanchez, Keith R. Mulholland, Nicholas J. Turner

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    Abstract

    The alkylation of amines with either alcohols or carboxylic acids represents a mild and safe alternative to the use of genotoxic alkyl halides and sulfonate esters. Here we report two complementary one-pot systems in which the reductive aminase (RedAm) from Aspergillus oryzae is combined with either (i) a 1° alcohol/alcohol oxidase (AO) or (ii) carboxylic acid/carboxylic acid reductase (CAR) to affect N-alkylation reactions. The application of both approaches has been exemplified with respect to substrate scope and also preparative scale synthesis. These new biocatalytic methods address issues facing alternative traditional synthetic protocols such as harsh conditions, overalkylation and complicated workup procedures.

    Original languageEnglish
    JournalJournal of the American Chemical Society
    Early online date2 Jan 2019
    DOIs
    Publication statusPublished - 23 Jan 2019

    Research Beacons, Institutes and Platforms

    • Manchester Institute of Biotechnology

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