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

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

36 Citations (Scopus)

47 Downloads (Pure)

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

Access to Document

10.1039/c7ob00283aLicence: CC BY

Download pdfFinal published version, 2.16 MBLicence: CC BY

Cite this

@article{1954c4a69075415b9a35317635dc5c98,

title = "The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems",

abstract = "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.",

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

year = "2017",

month = may,

day = "21",

doi = "10.1039/c7ob00283a",

language = "English",

volume = "15",

pages = "4086--4095",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "19",

}

TY - JOUR

T1 - The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems

AU - Gimenez, Diana

AU - Mooney, Caitlin A.

AU - Dose, Anica

AU - Sandford, Graham

AU - Coxon, Christopher R.

AU - Cobb, Steven L.

PY - 2017/5/21

Y1 - 2017/5/21

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/85021682422

U2 - 10.1039/c7ob00283a

DO - 10.1039/c7ob00283a

M3 - Article

C2 - 28470238

AN - SCOPUS:85021682422

SN - 1477-0520

VL - 15

SP - 4086

EP - 4095

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 19

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this