title: Rapid ligations with equimolar reactants in water with the potassium acyltrifluoroborate (KAT) amide formation.
abstract: The identification of fast, chemoselective bond-forming reactions is one of the major contemporary challenges in chemistry. We show that chemoselective amide-forming ligations of potassium acyltrifluoroborates (KATs) and O-carbamoylhydroxylamines proceed in the presence of all unprotected functional groups with a second-order rate constant of 20 M(-1) s(-1). PEG chains, lipids, biotin, and dyes were introduced onto an unprotected 31-mer peptide (a GLP-1 analogue) with equimolar ratios of reactants within minutes at 1 mM and within 1 h at 100 μM, even with Mw 20,000 PEG. This conjugation reaction provides a new approach to the synthesis of molecules such as protein-protein and protein-polymer conjugates.
authors.affiliation: Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH-Zürich, 8093 Zürich, Switzerland.
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Noda
authors.forename: Gábor
authors.initials: G
authors.lastname: Erős
authors.forename: Jeffrey W
authors.initials: JW
authors.lastname: Bode