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Synthesis of 7-Aminocoumarin by Buchwald–Hartwig Cross Coupling for Specific Protein Labeling in Living Cells

Authors

  • Xin Jin,

    1. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge MA, 02139 (USA), Fax: (+1) 617-253-7929
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    • These authors contributed equally to this work.

  • Chayasith Uttamapinant,

    1. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge MA, 02139 (USA), Fax: (+1) 617-253-7929
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    • These authors contributed equally to this work.

  • Prof. Dr. Alice Y. Ting

    Corresponding author
    1. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge MA, 02139 (USA), Fax: (+1) 617-253-7929
    • Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge MA, 02139 (USA), Fax: (+1) 617-253-7929
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Abstract

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PRIME time: We report the synthesis of a pH-insensitive blue fluorophore, 7-aminocoumarin, by using palladium- catalyzed Buchwald–Hartwig cross coupling. 7-Aminocoumarin can be used to tag recombinant proteins on the cell surface and inside living cells through PRIME (probe incorporation mediated by enzymes), and unlike 7-hydroxycoumarin, can be visualized in acidic organelles such as endosomes.

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