title: The role of boronic acids in accelerating condensation reactions of α-effect amines with carbonyls.
abstract: A broad palette of bioconjugation reactions are available for chemical biologists, but an area that still requires investigation is high-rate constant reactions. These are indispensable in certain applications, particularly for in vivo labelling. Appropriately positioned boronic acids accelerate normally sluggish Schiff base condensations of α-effect nucleophiles by five orders of magnitude - providing a new entry to the rare set of reactions that have a rate constant above 100 M(-1) s(-1) under physiological conditions. I summarize here a number of recent reports, including work from my own group, and outline a mechanistic picture that explains the differing behaviour of seemingly similar substrate classes.
authors.affiliation: Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056, Basel, Switzerland. dennis.gillingham@unibas.ch.
authors.forename: Dennis
authors.initials: D
authors.lastname: Gillingham