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Biocatalytic Asymmetric Synthesis of Optically Pure Aromatic Propargylic Amines Employing ω‐Transaminases
Author(s) -
Schmidt Nina G.,
Simon Robert C.,
Kroutil Wolfgang
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500086
Subject(s) - chemistry , amination , aspergillus terreus , propargyl , reductive amination , enantiomeric excess , chromobacterium violaceum , enantiomer , organic chemistry , enantioselective synthesis , stereochemistry , combinatorial chemistry , medicinal chemistry , catalysis , biochemistry , quorum sensing , food science , virulence , gene
The asymmetric reductive bio‐amination of prochiral aromatic propargyl ketones led to the corresponding amines in optically pure form ( ee >99%). The ( R )‐ as well as the ( S )‐enantiomers of the propargylic amines were obtained, employing either ( R )‐selective ω‐transaminases (ω‐TAs) originating from Arthrobacter sp. and Aspergillus terreus or an ( S )‐selective ω‐TA from Chromobacterium violaceum . The product propargylic amines were obtained with high conversions (up to 99%). To simplify product isolation, protection of the free amino group to the corresponding acetamides or benzamides was performed without loss of optical puritiy. The final products were isolated in moderate to good yields (33–67% over two steps) in optical pure form without additional purification steps. Although propargyl ketones are described in the literature to be irreversible inhibitors for aminotransferases, suitable ω‐transaminases were identified for the amination of these compounds.