Premium
Asymmetric Synthesis of Chiral Halogenated Amines using Amine Transaminases
Author(s) -
Dawood Ayad W. H.,
de Souza Rodrigo O. M. A.,
Bornscheuer Uwe T.
Publication year - 2018
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201701962
Subject(s) - amine gas treating , chemistry , enantioselective synthesis , isopropylamine , biocatalysis , combinatorial chemistry , organic chemistry , yield (engineering) , ketone , tertiary amine , catalysis , reaction mechanism , materials science , metallurgy
Amine transaminases (ATAs) are versatile and industrially relevant biocatalysts that catalyze the transfer of an amine group from a donor to an acceptor molecule. Asymmetric synthesis from a prochiral ketone is the most preferred route to the desired amine product, as it is obtainable in a theoretical yield of 100 %. In addition to the requirement of active and enantioselective ATAs, the choice of a suitable amine donor is also important to save costs and to avoid additional enzymes to shift the equilibrium and/or to recycle the cofactors. In this work, we identified suitable ( R )‐ and ( S )‐ATAs from Aspergillus fumigatus and Silicibacter pomeroyi , respectively, to afford a set of halogen‐substituted derivatives of brominated or chlorinated 1‐phenyl‐2‐propanamine, 4‐phenylbutan‐2‐amine, and 1‐(3‐pyridinyl)ethanamine. Optimization of the donor–acceptor ratio enabled application of isopropylamine as an amine donor, which resulted in high conversions and amines with 73–99 % ee .