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Issue 36, 2017
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N-Difluoromethyl-triazole as a constrained scaffold in peptidomimetics

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Abstract

The N-difluoromethyl triazolo-β-aza-ε-amino acid present in the core of peptides led to constrained conformations due to CH–F and NH–F interactions. Pseudotetrapeptides were obtained in excellent yields directly by click chemistry between azidodifluoroacetamides and alkynes, both linked to an amino acid. This work demonstrates that the N-difluoromethyltriazole scaffold can induce extended structures to β-strand mimics.

Graphical abstract: N-Difluoromethyl-triazole as a constrained scaffold in peptidomimetics

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Publication details

The article was received on 17 Feb 2017, accepted on 10 Apr 2017 and first published on 12 Apr 2017


Article type: Communication
DOI: 10.1039/C7CC01298E
Citation: Chem. Commun., 2017,53, 5024-5027
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    N-Difluoromethyl-triazole as a constrained scaffold in peptidomimetics

    M. Mamone, R. S. B. Gonçalves, F. Blanchard, G. Bernadat, S. Ongeri, T. Milcent and B. Crousse, Chem. Commun., 2017, 53, 5024
    DOI: 10.1039/C7CC01298E

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