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

35 Citations (Scopus)

98 Downloads (Pure)

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

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).",

author = "Diana Gimenez and Anica Dose and Robson, \{Nicholas L.\} and Graham Sandford and Cobb, \{Steven L.\} and Coxon, \{Christopher R.\}",

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T1 - 2,2,2-Trifluoroethanol as a solvent to control nucleophilic peptide arylation

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

N2 - 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).

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).

UR - https://www.scopus.com/pages/publications/85021680543

U2 - 10.1039/c7ob00295e

DO - 10.1039/c7ob00295e

M3 - Article

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AN - SCOPUS:85021680543

SN - 1477-0520

VL - 15

SP - 4081

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

Abstract

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