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Whole‐Cell Biocatalysts for Stereoselective C−H Amination Reactions
Author(s) -
Both Peter,
Busch Hanna,
Kelly Paul P.,
Mutti Francesco G.,
Turner Nicholas J.,
Flitsch Sabine L.
Publication year - 2016
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.201510028
Subject(s) - stereoselectivity , amination , biocatalysis , amine gas treating , chemistry , isopropyl , reductive amination , combinatorial chemistry , cascade , organic chemistry , stereochemistry , catalysis , reaction mechanism , chromatography
Enantiomerically pure chiral amines are ubiquitous chemical building blocks in bioactive pharmaceutical products and their synthesis from simple starting materials is of great interest. One of the most attractive strategies is the stereoselective installation of a chiral amine through C−H amination, which is a challenging chemical transformation. Herein we report the application of a multienzyme cascade, generated in a single bacterial whole‐cell system, which is able to catalyze stereoselective benzylic aminations with ee values of 97.5 %. The cascade uses four heterologously expressed recombinant enzymes with cofactors provided by the host cell and isopropyl amine added as the amine donor. The cascade presents the first example of the successful de novo design of a single whole‐cell biocatalyst for formal stereoselective C−H amination.