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DNA technology based on Click Chemistry

The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) is the most prominent example of a group of reactions named click-reactions. According to Sharpless` definition, these reactions are characterized by high yields, mild reaction conditions, and by their tolerance of a broad range of functional groups.[1] Typically, the reactions require simple or no workup or purification of the product. The most important characteristic of the CuAAC reaction is its unique bioorthogonality as neither azide nor terminal alkyne functional groups are generally present in natural systems.

The use of this method for DNA modification has been somewhat delayed by the fact that copper ions damage DNA, typically yielding strand breaks.[2] As these problems have now been overcome by the use of copper(I)-stabilizing ligands (e.g. tris(benzyltriazolylmethyl)amine, TBTA [3]), Carell et al. and Seela et al. discovered that the CuAAC reaction can be used to functionalize alkyne-modified DNA nucleobases with extremely high efficiency.[4,5]
Advantage of the baseclick platform:

  • Labeling by simple, efficient click reaction
  • High labeling yield (quantitative)
  • Allows introduction of sensitive labels (benign conditions)
  • Highly modular system (combinatorial approach)
  • Orthogonal to conventional methods
  • Bioorthogonal reaction (no azides or alkynes in natural systems)
  • labeling of all bases possible (G, A, C, T, U)
  • broad range of marker- and dye-azides, including conventional ones available
also adaptable to linking beads, microarrays, nanoparticles, peptides etc.
Baseclick provides innovative products to improve and enhance your research with the most advanced, highly efficient and easy-to-use technology, Click Chemistry. A big step forward for the research in fields like:

  • DNA and RNA labeling – incorporate our alkyne-phosphoramidites in your oligo and label it with our marker azides (single- or multi-labeling)
  • PCR assays, PCR primers and labeling of large fragments – use our alkyne-triphosphates in your nucleotide mixture and label your PCR-fragments with our marker azides or use our oligonucleotides as multi-labeled primers for pre- or post-synthetic modification
  • FISH probes and FISH experiments – use our alkyne-modified oligonucleotides and label them with our marker azides (pre- or post-hybridization)
  • PEGylation – introduce your preferred PEG-tag via click chemistry with outstanding yields and modularity
  • Flow cytometry, cell feeding, cell tracking and cell-based assays – feed your cells with our Ethynyl-dU (EdU) and subsequently detect newly synthesised DNA with our marker azides in Cell Proliferation or TUNEL assays
  • Microarrays – use our phosphoramidites, triphosphates or oligonucleotides to set up your microarray
  • Nanoparticles, Bioconjugation..
..and many other applications. Enhance your research with baseclick products.

   1   .C.W. Tornoe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064; V. V.            Rostovtsev, L. G. Green, V. V.       Fokin, K. B. Sharpless, Angew. Chem. 2002, 114,        2708-2711; Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
  2.   C. J. Burrows, J. G. Muller, Chem. Rev. 1998, 98, 1109 – 1151.

3.   T. R. Chan, R. Hilgraf, K. B. Sharpless, V. V. Fokin, Org. Lett. 2004, 6, 2853 – 2855.

  4.   J. Gierlich, G. A. Burley, P. M. E. Gramlich, D. M. Hammond, T. Carell, Org. Lett.               2006, 8, 3639-3642. F. Seela, V.  R. Sirivolu, Chem. Biodiversity 2006, 3, 509-514.
  5.   P. M. E. Gramlich, S. Warncke, J. Gierlich, T. Carell, Angew. Chem. 2008, 120, 3491–       3493; Angew. Chem. Int.  Ed. 2008, 47, 3442– 3444.