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      A strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems.

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          Abstract

          Selective chemical reactions that are orthogonal to the diverse functionality of biological systems have become important tools in the field of chemical biology. Two notable examples are the Staudinger ligation of azides and phosphines and the Cu(I)-catalyzed [3 + 2] cycloaddition of azides and alkynes ("click chemistry"). The Staudinger ligation has sufficient biocompatibility for performance in living animals but suffers from phosphine oxidation and synthetic challenges. Click chemistry obviates the requirement of phosphines, but the Cu(I) catalyst is toxic to cells, thereby precluding in vivo applications. Here we present a strain-promoted [3 + 2] cycloaddition between cyclooctynes and azides that proceeds under physiological conditions without the need for a catalyst. The utility of the reaction was demonstrated by selective modification of biomolecules in vitro and on living cells, with no apparent toxicity.

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          Author and article information

          Journal
          J Am Chem Soc
          Journal of the American Chemical Society
          American Chemical Society (ACS)
          0002-7863
          0002-7863
          Nov 24 2004
          : 126
          : 46
          Affiliations
          [1 ] Department of Chemistry, Howard Hughes Medical Institute, University of California, and Materials Sciences Division, Lawrence Berkeley National Laboratory, Berkeley, California 94720, USA.
          Article
          10.1021/ja044996f
          15547999
          fd273ce8-bfca-4194-aa5c-e1f76e206f15
          History

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