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

Diana Gimenez, Caitlin A. Mooney, Anica Dose, Graham Sandford, Christopher R. Coxon, Steven L. Cobb

Research output: Contribution to journalArticle

16 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4086-4095
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number19
Early online date21 Apr 2017
DOIs
Publication statusPublished - 21 May 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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