A Novel Allylic Anchor for Solid-Phase Synthesis—Synthesis of Protected and Unprotected O-Glycosylated Mucin-Type Glycopeptides

Authors

  • Dipl.-Chem. Oliver Seitz,

    1. Institut für Organische Chemie der Universität Mainz, J.-J. Becher-Weg 18–20, D-55099 Mainz (Germany), Telefax: Int. code + (6131)39-4786
    Search for more papers by this author
  • Prof. Dr. Horst Kunz

    Corresponding author
    1. Institut für Organische Chemie der Universität Mainz, J.-J. Becher-Weg 18–20, D-55099 Mainz (Germany), Telefax: Int. code + (6131)39-4786
    • Institut für Organische Chemie der Universität Mainz, J.-J. Becher-Weg 18–20, D-55099 Mainz (Germany), Telefax: Int. code + (6131)39-4786
    Search for more papers by this author

  • This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and the Boehringer-Ingelheim-Stiftung (stipend for O.S.). We are grateful to Professor C. Griesinger and Dr. R. Wechselberger, Universität Frankfurt/Main, for their help with multidimensional high-field NMR experiments.

  • Dedicated to Professor Hans Jeschkeit on the occasion of his 65th birthday

Abstract

original image

An efficient solid-phase synthesis of glycopeptides is achieved with the new anchor HYCRON, which combines an allylic ester with the flexible, solubilizing triethyleneglycol spacer. Acid- and base-stability of the allylic anchor enables both Fmoc and Boc strategies to be used. The partially protected glycopeptides can be cleaved from the support by Pd0 catalysis under virtually neutral conditions in high yields (about 95%) and purity (>95%). AMPS = aminomethylpolystyrene.

Ancillary