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Metal-Free, Regioselective Triazole Ligations that Deliver Locked cis Peptide Mimetics†

Authors

  • Ahsanullah M. Phil.,

    1. Leibniz Institute for Molecular Pharmacology (FMP), Robert-Rössle-Strasse 10, 13125 Berlin (Germany), Fax: (+49) 30-9406-2981
    2. Institute for Chemistry and Biochemistry, Free University Berlin, Takustrasse 3, 14195 Berlin (Germany)
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  • Peter Schmieder Dr.,

    1. Leibniz Institute for Molecular Pharmacology (FMP), Robert-Rössle-Strasse 10, 13125 Berlin (Germany), Fax: (+49) 30-9406-2981
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  • Ronald Kühne Dr.,

    1. Leibniz Institute for Molecular Pharmacology (FMP), Robert-Rössle-Strasse 10, 13125 Berlin (Germany), Fax: (+49) 30-9406-2981
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  • Jörg Rademann Prof. Dr.

    1. Leibniz Institute for Molecular Pharmacology (FMP), Robert-Rössle-Strasse 10, 13125 Berlin (Germany), Fax: (+49) 30-9406-2981
    2. Institute for Chemistry and Biochemistry, Free University Berlin, Takustrasse 3, 14195 Berlin (Germany)
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  • †

    We gratefully acknowledge the Higher Education Commission Pakistan and DAAD for a stipend granted to A. and the DFG (RA895/2, FOR 806, and SFB 765). J.R. thanks the Fonds der Chemischen Industrie for continuous support.

Abstract

Metal-free triazole turns: 1,5-Disubstituted peptidyl triazoles are obtained regioselectively from the 1,3-dipolar cycloaddition of peptidyl phosphoranes and azides. Peptide turns are thus formed that contain a conformationally locked cis peptide bond. Being regioselective and free of heavy metals, this reaction may find broad application in chemical biology and medicinal chemistry.

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DOI

10.1002/anie.200806390

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Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • 1,3-dipolar cycloaddition;
  • peptide mimetics;
  • phosphoranes;
  • structural biology;
  • triazoles

Publication History

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  • Manuscript Revised:

Funded by

  • Higher Education Commission Pakistan
  • DAAD
  • DFG
  • Fonds der Chemischen Industrie

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