Copper-free Click Chemistry

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Conventional "Click Chemistry" requires the presence of a Cu(I) catalyst that is toxic to most organisms and thus, prevents its use in many biological systems.

The novel Copper-free Click Chemistry is based on the reaction of a diarylcyclooctyne (DBCO) moiety with an azide-labeled reaction partner, known as strain-promoted alkyne azide cycloaddition (SPAAC). This new "Click Chemistry" is very fast at room temperature and does not require a cytotoxic Cu(I) catalyst. Diarylcyclooctynes are thermostable with very narrow and specific reactivity toward azides, resulting in almost quantitative yields of stable triazoles.

Bertozzi and coworkers used this reaction for in vivo applications[1],[2],[3],[4].

Cu(I)-free ligation reaction scheme: Diarylcyclooctyne-activated biomolecule A reacts with azide-activated biomolecule B without Cu(I) in aqueous conditions to form a stable triazole

   Product features and benefits:

  • Biocompatibility – no cytotoxic Copper catalyst required
  • Mild conditions – conjugation in aqueous buffered media and at low temperature
  • Stability – DBCO and azide moieties are long term stable
  • Efficiency – formation of a stable triazole in quantitative yield
  • Specificity and Bioorthogonality – azide reacts only with DBCO in the presence of -NH2, -SH, -COOH and other protein functionalities

   Jena Bioscience's new product line of Copper-free Click Chemistry contains:

  • Non-Fluorescent Azides
  • Biotin Azides
  • PEG and Spacer Azides
  • Azides of Amino Acids
  • Azides of Fluorescent Dyes

Also available: Reagents for conventional Copper(I)-catalyzed Click Reactions, such as
Ethynyl-U, Ethynyl-dU, Ethynyl-dUTP and more...

Selected References:
[1] Bertozzi et al. (2006) A comparative study of bioorthogonal reactions with azides. Chem. Biol. 1:644.
[2] Bertozzi et al. (2007) Copper-free click chemistry for dynamic in vivo imaging. Proc. Natl. Acad. Sci. U.S.A. 104:16793.
[3] Bertozzi et al. (2009) Biorthogonal Chemistry: Fishing for selectivity in a sea of functionality. Angew. Chem. Int. Ed. 48:6974.
[4] Bertozzi et al. (2010) Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones. J. Am. Chem. Soc. 132:3688.


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