Metal-Free Triazole Formation as a Tool for Bioconjugation

Authors

  • Sander S. van Berkel,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands, Fax: (+31) 24-365-3393
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    • These authors contributed equally to this work.

  • A. (Ton) J. Dirks,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands, Fax: (+31) 24-365-3393
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    • These authors contributed equally to this work.

  • Marjoke F. Debets,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands, Fax: (+31) 24-365-3393
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  • Floris L. van Delft Dr.,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands, Fax: (+31) 24-365-3393
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  • Jeroen J. L. M. Cornelissen Dr.,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands, Fax: (+31) 24-365-3393
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  • Roeland J. M. Nolte Prof.,

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands, Fax: (+31) 24-365-3393
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  • Floris P. J. T. Rutjes Prof.

    1. Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, 6525 ED Nijmegen, The Netherlands, Fax: (+31) 24-365-3393
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Abstract

original image

Who needs copper? There is a strong demand for ligation reactions that proceed spontaneously, selectively, and under physiological conditions. To meet these criteria, we used trifluoromethyl-substituted oxanorbornadienes in reactions with various azides, and achieved an elegant tandem [3+2] cycloaddition–retro-Diels–Alder reaction that forms stable 1,2,3-triazole-linked bioconjugates (see scheme).

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