The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems12. Issue 19 (4th May 2017)

• Record Type: Journal Article
• Authors: Gimenez, Diana; Mooney, Caitlin A.; Dose, Anica; Sandford, Graham; Coxon, Christopher R.; Cobb, Steven L.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 19(2017)
• Page Start: 4086
• Page End: 4095
• Publication Date: 2017-05-04
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c7ob00283a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A one-step peptide-modification using perfluoroheteroaromatics can deliver enhanced proteolytic stability in pharmaceutically relevant peptides such as oxytocin. Abstract : The perfluoroheteroaromatic reagent pentafluoropyridine has proved to be a highly reactive electrophile, undergoing SN Ar 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.