2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation

Diana Gimenez, Anica Dose, Nicholas L. Robson, Graham Sandford, Steven L. Cobb, Christopher R. Coxon

Research output: Contribution to journalArticle

17 Citations (Scopus)
1 Downloads (Pure)

Abstract

The SNAr arylation of peptides with perfluoroaromatics provides a route by which to install a useful chemical handle that enables both 19F-NMR analysis and further chemical modification. However, chemo-selective arylation in peptides containing multiple nucleophilic side chains currently presents a challenge to the field. Herein, we demonstrate that employing 2,2,2-trifluoroethanol (TFE) as a solvent in peptide SNAr reactions significantly improves nucleophile-selectivity when compared to N,N′-dimethylformamide (DMF).

Original languageEnglish
Pages (from-to)4081-4085
Number of pages5
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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