Open AccessBiocatalytic N-Alkylation of Amines Using Either Primary Alcohols or Carboxylic Acids via Reductive Aminase Cascades
Author(s) -
Jeremy I. Ramsden,
Rachel S. Heath,
Sasha R. Derrington,
Sarah L. Montgomery,
Juan MangasSánchez,
Keith R. Mulholland,
Nicholas J. Turner
Publication year - 2019
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.8b11561
Subject(s) - chemistry , alkylation , alcohol , carboxylic acid , organic chemistry , primary (astronomy) , alkyl , primary alcohol , halide , alcohol oxidase , substrate (aquarium) , oxidase test , combinatorial chemistry , enzyme , catalysis , biochemistry , pichia pastoris , physics , oceanography , astronomy , geology , gene , recombinant dna
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.
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