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

Gimenez, D and Dose, A and Robson, NL and Sandford, G and 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 & Biomolecular Sciences
Publisher: Royal Society of Chemistry
Date Deposited: 16 May 2017 09:35
Last Modified: 16 May 2017 09:35
DOI or Identification number: 10.1039/C7OB00295E
URI: http://researchonline.ljmu.ac.uk/id/eprint/6425

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