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Direct Alkylation of Amines with Primary and Secondary Alcohols through Biocatalytic Hydrogen Borrowing
Author(s) -
Montgomery Sarah L.,
MangasSanchez Juan,
Thompson Matthew P.,
Aleku Godwin A.,
Dominguez Beatriz,
Turner Nicholas J.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201705848
Subject(s) - chemistry , primary (astronomy) , alkylation , biocatalysis , alcohol , alcohol dehydrogenase , aspergillus oryzae , organic chemistry , primary alcohol , alcohol oxidation , enzyme , catalysis , combinatorial chemistry , ionic liquid , physics , astronomy
The reductive aminase from Aspergillus oryzae ( Asp RedAm) was combined with a single alcohol dehydrogenase (either metagenomic ADH‐150, an ADH from Sphingobium yanoikuyae (SyADH), or a variant of the ADH from Thermoanaerobacter ethanolicus ( Te SADH W110A)) in a redox‐neutral cascade for the biocatalytic alkylation of amines using primary and secondary alcohols. Aliphatic and aromatic secondary amines were obtained in up to 99 % conversion, as well as chiral amines directly from the racemic alcohol precursors in up to >97 % ee , releasing water as the only byproduct.