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Cyclative Cleavage through Dipolar Cycloaddition: Polymer-Bound Azidopeptidylphosphoranes Deliver Locked cis-Triazolylcyclopeptides as Privileged Protein Binders

Authors

  • Ahsanullah,

    1. Leibniz Institute of Molecular Pharmacology (FMP), Robert-Rössle-Strasse 10, 13125 Berlin (Germany)
    2. Institute for Chemistry and Biochemistry, Free University Berlin, Takustrasse 3, 14195 Berlin (Germany)
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  • Jörg Rademann Prof. Dr.

    1. Medicinal Chemistry, Institute of Pharmacy, Leipzig University, Brüderstrasse 34, 04103 Leipzig (Germany), Fax: (+49) 341-97378
    2. Leibniz Institute of Molecular Pharmacology (FMP), Robert-Rössle-Strasse 10, 13125 Berlin (Germany)
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  • We gratefully acknowledge the Higher Education Commission (HEC) of Pakistan and the Deutsche Akademische Austauschdienst (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

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Support and guidance: Azidopeptidyl phosphoranes on a solid support react very efficiently through cyclative cleavage to yield cyclopeptides with an incorporated triazole ring. The solid support is advantageous as cyclization is favored strongly over oligomerization reactions and thus only cyclized products are released.

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