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Issue 19, 2017
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The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems

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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.

Graphical abstract: The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems

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Publication details

The article was received on 06 Feb 2017, accepted on 19 Apr 2017 and first published on 21 Apr 2017


Article type: Paper
DOI: 10.1039/C7OB00283A
Citation: Org. Biomol. Chem., 2017,15, 4086-4095
  • Open access: Creative Commons BY license
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    The application of perfluoroheteroaromatic reagents in the preparation of modified peptide systems

    D. Gimenez, C. A. Mooney, A. Dose, G. Sandford, C. R. Coxon and S. L. Cobb, Org. Biomol. Chem., 2017, 15, 4086
    DOI: 10.1039/C7OB00283A

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