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

doi:10.1039/c7ob00295e

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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Abstract

The S_NAr 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 S_NAr reactions significantly improves nucleophile-selectivity when compared to N,N′-dimethylformamide (DMF).

Original language	English
Pages (from-to)	4081-4085
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	19
Early online date	21 Apr 2017
DOIs	https://doi.org/10.1039/c7ob00295e
Publication status	Published - 21 May 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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,N′-dimethylformamide (DMF).",

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AU - Gimenez, Diana

AU - Dose, Anica

AU - Robson, Nicholas L.

AU - Sandford, Graham

AU - Cobb, Steven L.

AU - Coxon, Christopher R.

PY - 2017/5/21

Y1 - 2017/5/21

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AB - 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).

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U2 - 10.1039/c7ob00295e

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EP - 4085

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 19

ER -

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

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