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The Combination of Prolinoamino Acids and Cyclopropylamino Acids Leads to Fully Functionalized, Stable β-Turns in Water

Authors

  • Dr. Karine Guitot,

    1. UPMC Université Paris 06, Laboratoire des BioMolécules, UMR 7203 and FR2769, 4, Place Jussieu, 75005 Paris (France), Fax: (+33) 1-44322402
    2. Ecole Normale Superieure, Département de Chimie, 24, rue Lhomond, 75005 Paris (France)
    3. UMR 7203 CNRS-UPMC-ENS
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  • Dr. Maud Larregola,

    1. UPMC Université Paris 06, Laboratoire des BioMolécules, UMR 7203 and FR2769, 4, Place Jussieu, 75005 Paris (France), Fax: (+33) 1-44322402
    2. Ecole Normale Superieure, Département de Chimie, 24, rue Lhomond, 75005 Paris (France)
    3. UMR 7203 CNRS-UPMC-ENS
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  • Dr. Tarun K. Pradhan,

    1. Université de Reims Champagne-Ardenne, UMR-CNRS 6229, Institut de Chimie Moléculaire de Reims, BP 1039, 51687, Reims Cedex 02 (France)
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  • Dr. Jean-Luc Vasse,

    1. Université de Reims Champagne-Ardenne, UMR-CNRS 6229, Institut de Chimie Moléculaire de Reims, BP 1039, 51687, Reims Cedex 02 (France)
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  • Prof. Solange Lavielle,

    1. UPMC Université Paris 06, Laboratoire des BioMolécules, UMR 7203 and FR2769, 4, Place Jussieu, 75005 Paris (France), Fax: (+33) 1-44322402
    2. Ecole Normale Superieure, Département de Chimie, 24, rue Lhomond, 75005 Paris (France)
    3. UMR 7203 CNRS-UPMC-ENS
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  • Prof. Philippe Bertus,

    1. Université du Maine, UMR-CNRS 6011, Unité de Chimie Organique Moléculaire et Macromoléculaire, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9 (France)
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  • Prof. Jan Szymoniak,

    1. Université de Reims Champagne-Ardenne, UMR-CNRS 6229, Institut de Chimie Moléculaire de Reims, BP 1039, 51687, Reims Cedex 02 (France)
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  • Prof. Olivier Lequin,

    Corresponding author
    1. UPMC Université Paris 06, Laboratoire des BioMolécules, UMR 7203 and FR2769, 4, Place Jussieu, 75005 Paris (France), Fax: (+33) 1-44322402
    2. Ecole Normale Superieure, Département de Chimie, 24, rue Lhomond, 75005 Paris (France)
    3. UMR 7203 CNRS-UPMC-ENS
    • UPMC Université Paris 06, Laboratoire des BioMolécules, UMR 7203 and FR2769, 4, Place Jussieu, 75005 Paris (France), Fax: (+33) 1-44322402
    Search for more papers by this author
  • Prof. Philippe Karoyan

    Corresponding author
    1. UPMC Université Paris 06, Laboratoire des BioMolécules, UMR 7203 and FR2769, 4, Place Jussieu, 75005 Paris (France), Fax: (+33) 1-44322402
    2. Ecole Normale Superieure, Département de Chimie, 24, rue Lhomond, 75005 Paris (France)
    3. UMR 7203 CNRS-UPMC-ENS
    • UPMC Université Paris 06, Laboratoire des BioMolécules, UMR 7203 and FR2769, 4, Place Jussieu, 75005 Paris (France), Fax: (+33) 1-44322402
    Search for more papers by this author

Abstract

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Tight turns: Peptide mimics based on combinations of cis-3-prolinoamino acids (prolinohomotryptophan) and (Z)-2,3-methanoamino acids (c3Arg or c3Lys) form stable β-turns in water. This combination of constraints allows one to mimic turns with side chain conformations not accessible with the previously reported strategy involving combinations of prolinoamino acids and N-methylamino acids.

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