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Toward Fully Synthetic N-Linked Glycoproteins

Authors

  • Justin S. Miller Dr.,

    1. Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA, Fax: (+1) 212-772-8691
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  • Vadim Y. Dudkin Dr.,

    1. Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA, Fax: (+1) 212-772-8691
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  • Gholson J. Lyon,

    1. Laboratory of Synthetic Protein Chemistry, The Rockefeller University, 1230 York Avenue, New York, NY 10021, USA
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  • Tom W. Muir Prof.,

    1. Laboratory of Synthetic Protein Chemistry, The Rockefeller University, 1230 York Avenue, New York, NY 10021, USA
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  • Samuel J. Danishefsky Prof.

    1. Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA, Fax: (+1) 212-772-8691
    2. Department of Chemistry, Columbia University, Havemeyer Hall, New York, NY 10027, USA
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  • This work was supported by the NIH (AI16943). The receipt of a Pfizer Award to S.J.D. for Creative Work in Organic Synthesis is gratefully acknowledged. We thank Drs. Andrzej Zatorski and Ulrich Iserloh for the preparation of starting materials and for helpful discussions, and Dr. George Sukenick and Ms. Sylvi Rusli (NMR Core Facility, CA-02848) for mass spectral analyses.

Abstract

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Beträchtliche Mengen vollsynthetischer homogener N-verknüpfter Glycopeptide sind durch eine konvergente und flexible Methode zugänglich – nur vier Syntheseschritte sind erforderlich, um die natürlich verknüpften Glycopeptide in hohen Ausbeuten zu erhalten: Der Aminierung eines freien Glycans schließt sich eine Acylierung des neu eingeführten N-Atoms mit dem Asparaginrest eines Peptids an; native chemische Ligation schließt den Prozess ab (siehe Schema).

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