Premium
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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201705848
Subject(s) - chemistry , alkylation , primary (astronomy) , biocatalysis , alcohol , primary alcohol , organic chemistry , alcohol dehydrogenase , aspergillus oryzae , alcohol oxidation , amine gas treating , enzyme , combinatorial chemistry , catalysis , reaction mechanism , 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.