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

Author:
Ramsden, Jeremy I., Heath, Rachel S., Derrington, Sasha R., Montgomery, Sarah L., Mangas-Sanchez, Juan, Mulholland, Keith R., Turner, Nicholas J.
Source:
Journal of the American Chemical Society 2019 v.141 no.3 pp. 1201-1206
ISSN:
1520-5126
Subject:
Aspergillus oryzae, alcohol oxidase, alkylation, amines, biocatalysis, carboxylic acids, esters, mutagens, organic halogen compounds, sulfonates
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.
Agid:
6271621