The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems

Diana Gimenez; Caitlin A. Mooney; Anica Dose; Graham Sandford; Christopher R. Coxon; Steven L. Cobb

doi:10.1039/c7ob00283a

The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems

Diana Gimenez, Caitlin A. Mooney, Anica Dose, Graham Sandford, Christopher R. Coxon^*, Steven L. Cobb

^*Corresponding author for this work

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Abstract

The perfluoroheteroaromatic reagent pentafluoropyridine has proved to be a highly reactive electrophile, undergoing S_NAr arylation reactions in the presence of a range of nucleophilic peptide side chains (i.e. cysteine, tyrosine, serine and lysine) under mild conditions. Moreover, we have shown how one-step peptide-modification using perfluoroheteroaromatics can deliver enhanced proteolytic stability in pharmaceutically-relevant peptides such as oxytocin.

Original language	English
Pages (from-to)	4086-4095
Number of pages	10
Journal	Organic and Biomolecular Chemistry
Volume	15
Issue number	19
Early online date	21 Apr 2017
DOIs	https://doi.org/10.1039/c7ob00283a
Publication status	Published - 21 May 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Coxon, Christopher R.

AU - Cobb, Steven L.

PY - 2017/5/21

Y1 - 2017/5/21

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AB - The perfluoroheteroaromatic reagent pentafluoropyridine has proved to be a highly reactive electrophile, undergoing SNAr arylation reactions in the presence of a range of nucleophilic peptide side chains (i.e. cysteine, tyrosine, serine and lysine) under mild conditions. Moreover, we have shown how one-step peptide-modification using perfluoroheteroaromatics can deliver enhanced proteolytic stability in pharmaceutically-relevant peptides such as oxytocin.

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U2 - 10.1039/c7ob00283a

DO - 10.1039/c7ob00283a

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AN - SCOPUS:85021682422

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JO - Organic and Biomolecular Chemistry

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ER -

The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems

Abstract

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