- Rapid ligations with equimolar reactants in water with the potassium acyltrifluoroborate (KAT) amide formation.
Rapid ligations with equimolar reactants in water with the potassium acyltrifluoroborate (KAT) amide formation.
Journal of the American Chemical Society (2014-04-02)
Hidetoshi Noda, Gábor Erős, Jeffrey W Bode
PMID24684235
ABSTRAKT
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.