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

Gimenez, D, Dose, A, Robson, NL, Sandford, G, Cobb, SL and Coxon, CR (2017) 2,2,2-Trifluoroethanol as a Tool to Control Nucleophilic Peptide Arylation. Organic & Biomolecular Chemistry. ISSN 1477-0520

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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).

Item Type:	Article
Uncontrolled Keywords:	0304 Medicinal And Biomolecular Chemistry, 0305 Organic Chemistry, 1115 Pharmacology And Pharmaceutical Sciences
Subjects:	Q Science > QD Chemistry
Divisions:	Pharmacy and Biomolecular Sciences
Publisher:	Royal Society of Chemistry
Date of acceptance:	19 April 2017
Date of first compliant Open Access:	16 May 2017
Date Deposited:	16 May 2017 09:35
Last Modified:	04 Sep 2021 11:35
DOI or ID number:	10.1039/C7OB00295E
URI:	https://ljmu-9.eprints-hosting.org/id/eprint/6425

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