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Nucleophilic Catalysis of Oxime Ligation
Author(s) -
Dirksen Anouk,
Hackeng Tilman M.,
Dawson Philip E.
Publication year - 2006
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.200602877
Subject(s) - chemistry , oxime , nucleophile , imine , aniline , combinatorial chemistry , biomolecule , organic chemistry , catalysis , medicinal chemistry , photochemistry , polymer chemistry , biochemistry
Aniline acts as a nucleophilic catalyst of oxime ligation in aqueous solution through formation of the orange‐colored intermediate. The method is demonstrated by acceleration of the oxime ligation of peptides at pH 4.5 and pH 7, which extends the scope of this reaction to conditions relevant for the bioconjugation of macromolecules (see scheme).