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Synthesis of a Biologically Active Triazole-Containing Analogue of Cystatin A Through Successive Peptidomimetic Alkyne–Azide Ligations

Authors

  • Dr. Ibai E. Valverde,

    1. Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans cedex 2 (France)
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  • Dr. Fabien Lecaille,

    1. Protéases et Vectorisation Pulmonaires, INSERM U618, Université François Rabelais, 10, boulevard Tonnellé, 37032 Tours cedex (France)
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  • Prof. Dr. Gilles Lalmanach,

    1. Protéases et Vectorisation Pulmonaires, INSERM U618, Université François Rabelais, 10, boulevard Tonnellé, 37032 Tours cedex (France)
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  • Dr. Vincent Aucagne,

    Corresponding author
    1. Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans cedex 2 (France)
    • Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans cedex 2 (France)
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  • Dr. Agnès F. Delmas

    Corresponding author
    1. Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans cedex 2 (France)
    • Centre de Biophysique Moléculaire, CNRS UPR 4301, Rue Charles Sadron, 45071 Orléans cedex 2 (France)
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  • The Région Centre council is gratefully acknowledged for financial support (FibroCat project and PhD fellowship for I.E.V.). We thank the CBM spectrometric platforms, and in particular Guillaume Gabant, for recording most of the MALDI-TOF spectra, Hervé Meudal for the NMR spectra, and Dr. Sandrine Villette for her help in the circular dichroism experiments. We thank Dr. Stéphane Bourg (molecular modeling lab, University of Orleans-CNRS FR 2708 research federation) for DFT calculations.

Abstract

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„Klick“-Protein: Drei ungeschützte Peptidfragmente wurden nacheinander über die CuI-katalysierte Cycloaddition von Aziden und terminalen Alkinen ligiert. Diese peptidomimetische Triazolligation (PTL, siehe Schema) ist eine neue Methode für die chemische Synthese bioaktiver Proteine und wurde für die Synthese eines triazolhaltigen Analogons des aus 97 Aminosäuren bestehenden Proteins Cystatin A genutzt.

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