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Copper-free click chemistry for dynamic in vivo imaging.

Proceedings of the National Academy of Sciences of the United States of America

Animals, Biological Transport, CHO Cells, Catalysis, Cell Survival, Chemistry, Organic, methods, Copper, metabolism, Cricetinae, Cricetulus, Endocytosis, Humans, Hydrocarbons, Cyclic, chemical synthesis, chemistry, Hydrocarbons, Fluorinated, Imaging, Three-Dimensional, Jurkat Cells, Kinetics, Polysaccharides, Proteins, Time Factors

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      Abstract

      Dynamic imaging of proteins in live cells is routinely performed by using genetically encoded reporters, an approach that cannot be extended to other classes of biomolecules such as glycans and lipids. Here, we report a Cu-free variant of click chemistry that can label these biomolecules rapidly and selectively in living systems, overcoming the intrinsic toxicity of the canonical Cu-catalyzed reaction. The critical reagent, a substituted cyclooctyne, possesses ring strain and electron-withdrawing fluorine substituents that together promote the [3 + 2] dipolar cycloaddition with azides installed metabolically into biomolecules. This Cu-free click reaction possesses comparable kinetics to the Cu-catalyzed reaction and proceeds within minutes on live cells with no apparent toxicity. With this technique, we studied the dynamics of glycan trafficking and identified a population of sialoglycoconjugates with unexpectedly rapid internalization kinetics.

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      Journal
      17942682
      2040404
      10.1073/pnas.0707090104

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