Get access

Helical Oligomers of Thiazole-Based γ-Amino Acids: Synthesis and Structural Studies

Authors

  • Loïc Mathieu,

    1. Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)
    Search for more papers by this author
    • These authors contributed equally to the work.

  • Dr. Baptiste Legrand,

    1. Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)
    Search for more papers by this author
    • These authors contributed equally to the work.

  • Cheng Deng,

    1. Laboratoire de Chimie-Physique Macromoléculaire, LCPM-UMR 7568 CNRS Université de Lorraine, 1 rue Grandville, 54001 Nancy Cedex 1 (France)
    Search for more papers by this author
  • Dr. Lubomir Vezenkov,

    1. Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)
    Search for more papers by this author
  • Emmanuel Wenger,

    1. Laboratoire de Cristallographie, Résonance Magnétique et Modélisation, UMR 7063 CNRS Université de Lorraine, Boulevard des Aiguillettes, 54506 Vandoeuvre-lès-Nancy Cedex (France)
    Search for more papers by this author
  • Dr. Claude Didierjean,

    1. Laboratoire de Cristallographie, Résonance Magnétique et Modélisation, UMR 7063 CNRS Université de Lorraine, Boulevard des Aiguillettes, 54506 Vandoeuvre-lès-Nancy Cedex (France)
    Search for more papers by this author
  • Dr. Muriel Amblard,

    1. Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)
    Search for more papers by this author
  • Dr. Marie-Christine Averlant-Petit,

    1. Laboratoire de Chimie-Physique Macromoléculaire, LCPM-UMR 7568 CNRS Université de Lorraine, 1 rue Grandville, 54001 Nancy Cedex 1 (France)
    Search for more papers by this author
  • Dr. Nicolas Masurier,

    1. Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)
    Search for more papers by this author
  • Prof. Vincent Lisowski,

    1. Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)
    Search for more papers by this author
  • Prof. Jean Martinez,

    1. Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)
    Search for more papers by this author
  • Dr. Ludovic T. Maillard

    Corresponding author
    1. Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)
    • Institut des Biomolécules Max Mousseron, UMR 5247, CNRS, Universités Montpellier I et II, UFR des Sciences Pharmaceutiques et Biologiques, 15 Avenue Charles Flahault, 34093 Montpellier Cedex 5 (France)

    Search for more papers by this author

  • We thank the IBMM, the CNRS, and the University of Montpellier 1 for financial support and the University of Lorraine for NMR and XRD facilities.

Abstract

original image

9-Helix: 4-Amino(methyl)-1,3-thiazole-5-carboxylic acids (ATCs) were synthesized as new γ-amino acid building blocks. The structures of various ATC oligomers were analyzed in solution by CD and NMR spectroscopy and in the solid state by X-ray crystallography. The ATC sequences adopted a well-defined 9-helix structure in the solid state and in aprotic and protic organic solvents as well as in aqueous solution.

Ancillary