2,2,2-Trifluoroethanol as a Tool to Control Nucleophilic Peptide Arylation

Gimenez, D.; Dose, A.; Robson, N.L.; Sandford, G.; Cobb, S.L.; Coxon, C.R.

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,Nʹ-dimethylformamide (DMF).

Citation

Gimenez, D., Dose, A., Robson, N., Sandford, G., Cobb, S., & Coxon, C. (2017). 2,2,2-Trifluoroethanol as a Tool to Control Nucleophilic Peptide Arylation. Organic and Biomolecular Chemistry, 15(19), 4081-4085. https://doi.org/10.1039/c7ob00295e

• Journal Article Type: Article
• Acceptance Date: Apr 19, 2017
• Online Publication Date: Apr 21, 2017
• Publication Date: May 21, 2017
• Deposit Date: Apr 24, 2017
• Publicly Available Date: Apr 26, 2017
• Journal: Organic and Biomolecular Chemistry
• Print ISSN: 1477-0520
• Electronic ISSN: 1477-0539
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 15
• Issue: 19
• Pages: 4081-4085
• DOI: https://doi.org/10.1039/c7ob00295e