Although aniline is known to catalyze the oxime ligation reaction in physiological conditions, it suffers from slow reaction kinetics, specifically when a ketone is being used or when transoximization is performed. Here, a new catalyst is introduced that is up to 40 times more efficient than aniline. The new catalyst is used to site-specifically label an aldehyde-functionalized protein through oxime ligation, and its kinetics are compared to reaction with aniline. Next, a protein is site-specifically labeled in crude cell lysate, captured onto a solid surface and then kinetic of the release of the immobilized protein via transoximization is analyzed. Our results show that the new catalyst can release and label 40 times more protein than aniline could in 3 h. It is expected that this new catalyst will have a profound impact on bioconjugation research, where oxime ligation or transoximization is used.

New highly efficient catalyst for oxime ligation and transoximization: Applications in direct protein enrichment and labeling via enzymatic modification

243rd National Meeting (2012)

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