Article
Mechanism-inspired engineering of phenylalanine aminomutase for enhanced β-regioselective asymmetric amination of cinnamates.
Angewandte Chemie (International ed. in English) - 9 Jan 2012
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
Abstract excerpt
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.
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