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A Single Residue Influences the Reaction Mechanism of Ammonia Lyases and Mutases
Author(s) -
Bartsch Sebastian,
Bornscheuer Uwe T.
Publication year - 2009
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.200900337
Subject(s) - residue (chemistry) , chemistry , ammonia , friedel–crafts reaction , reaction mechanism , stereochemistry , organic chemistry , catalysis
Abstract All ways lead to Rome? Computer modeling and kinetic measurements identified a distinct residue in Phe/Tyr ammonia lyases (PAL/TAL) which controls whether the Friedel–Crafts or an E 1 cB reaction mechanism takes place. Hence, Glu484 in pc PAL favors the Friedel–Crafts reaction (see picture, MIO=4‐methylidene imidazol‐5‐one) whereas an Asn in TAL gives an elimination reaction. These mechanistic investigations also reveal activity of a PAL mutant and a TAL towards an amino alcohol.