Nucleophilic catalysis of oxime ligation

Abstract

(Chemical Equation Presented) 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). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.