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Mechanism‐Inspired Engineering of Phenylalanine Aminomutase for Enhanced β‐Regioselective Asymmetric Amination of Cinnamates
Author(s) -
Wu Bian,
Szymański Wiktor,
Wybenga Gjalt G.,
Heberling Matthew M.,
Bartsch Sebastian,
de Wildeman Stefaan,
Poelarends Gerrit J.,
Feringa Ben L.,
Dijkstra Bauke W.,
Janssen Dick B.
Publication year - 2012
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.201106372
Subject(s) - regioselectivity , amination , chemistry , cinnamates , carboxylate , stereochemistry , computer science , organic chemistry , catalysis
Turn to switch : A mutant of phenylalanine aminomutase was engineered that can catalyze the regioselective amination of cinnamate derivatives (see scheme, red) to, for example, β‐amino acids. This regioselectivity, along with the X‐ray crystal structures, suggests two distinct carboxylate binding modes differentiated by C β C ipso bond rotation, which determines if β‐ (see scheme) or α‐addition takes place.