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Going live with click chemistry
Date:10/30/2007

copper-catalyzed azide-alkyne reaction that makes it possible for certain chemical building blocks to click together in an irreversible linkage. Since its introduction in 2001 by the Nobel laureate chemist Karl Barry Sharpless of the Scripps Research Institute, the copper-catalyzed azide-alkyne reaction has proven extremely valuable for attaching small molecular probes to various biomolecules in a test tube or on fixed cells. However, its use for biomolecule labeling in live cells or organisms is prohibited by the requirement of a cyotoxic copper catalyst.

For the past several years, Bertozzi has been developing new techniques for studying glycans. Even though glycans are ubiquitous on the surfaces of most cells and play a critical role in intercellular communications, methods for studying them have lagged behind other biomolecules.

Glycans mediate a variety of cell surface recognition events such as bacterial and viral binding to host cells and leukocyte adhesion during an inflammatory response, said Bertozzi. In addition to their cell surface roles, glycans can regulate many intracellular processes, including trafficking of proteins to the lysosome and transcription and translation.

There is great scientific interest in monitoring the dynamics of glycans as they move about within cells and on the cell surface, but the means to tag glycans with imaging probes has been lacking, thereby prohibiting such studies. Bertozzi and her coworkers had previously shown that glycans can be metabolically labeled with azides, permitting their chemical tagging with imaging probes through click chemistry, but the cytotoxicity of the click reaction would not allow dynamic imaging of live cells.

To apply click chemistry to glycans, Bertozzi and her colleagues designed a new reagent called difluorinated cyclooctyne or DIFO, that reacts with azides rapidly at physiological temperatures without the need for a toxic catalyst.

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Contact: Lynn Yarris
lcyarris@lbl.gov
510-486-5375
DOE/Lawrence Berkeley National Laboratory  
Source:Eurekalert

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