The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems??

Organic & Biomolecular Chemistry Pub Date: 2017-04-21 DOI: 10.1039/C7OB00283A

Abstract

The perfluoroheteroaromatic reagent pentafluoropyridine has proved to be a highly reactive electrophile, undergoing SNAr arylation reactions in the presence of a range of nucleophilic peptide side chains (i.e. cysteine, tyrosine, serine and lysine) under mild conditions. Moreover, we have shown how one-step peptide-modification using perfluoroheteroaromatics can deliver enhanced proteolytic stability in pharmaceutically-relevant peptides such as oxytocin.

Graphical abstract: The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems
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