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Two-Color Glycan Labeling of Live Cells by a Combination of Diels–Alder and Click Chemistry

Authors

  • Dipl.-Chem. Andrea Niederwieser,

    1. University of Konstanz, Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), 78457 Konstanz (Germany)
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  • M. Sc. Anne-Katrin Späte,

    1. University of Konstanz, Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), 78457 Konstanz (Germany)
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  • Dr. Long Duc Nguyen,

    1. Institut für Biochemie und Molekularbiologie, CBF, Charité Universitätsmedizin, 14195 Berlin-Dahlem (Germany)
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  • M. Sc. Christian Jüngst,

    1. University of Konstanz, Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), 78457 Konstanz (Germany)
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  • Prof. Dr. Werner Reutter,

    1. Institut für Biochemie und Molekularbiologie, CBF, Charité Universitätsmedizin, 14195 Berlin-Dahlem (Germany)
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  • Prof. Dr. Valentin Wittmann

    Corresponding author
    1. University of Konstanz, Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), 78457 Konstanz (Germany)
    • University of Konstanz, Department of Chemistry and Konstanz Research School Chemical Biology (KoRS-CB), 78457 Konstanz (Germany)
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  • This work was supported by the Deutsche Forschungsgemeinschaft (SFB 969), the University of Konstanz, the Konstanz Research School Chemical Biology, the Wilhelm Sander-Stiftung (L.D.N., W.R.), and the Sonnenfeld-Stiftung, Berlin (L.D.N.). We thank Prof. M. Wießler for helpful discussions regarding the Diels–Alder chemistry and the Bioimaging Center of the University of Konstanz and Prof. A. Zumbusch for providing the fluorescence microscopy instrumentation.

Abstract

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One is not enough: Terminal alkenes are used as chemical reporters and ligation partners for 1,2,4,5-tetrazines in a Diels–Alder reaction with inverse electron demand (DARinv). Combination with strain-promoted azide–alkyne cycloaddition (SPAAC) allows the visualization of two different glycan structures in one experiment.

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