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Click Chemistry

Click chemistry is a two-step process that uses quantitative chemical reactions of alkyne and azide moieties to create covalent carbon-heteroatom bonds between biochemical species.1 The reaction uses copper(I) as a catalyst and forms a 1,2,3-triazole between an azide and terminal alkyne.2 The technology is reliable and stable which makes it an ideal oligonucleotide labeling method.

The benefits of click chemistry include1:

  • Reaction occurs in aqueous solution and at room temperature
  • Stability toward H2O, O2, and most organic synthesis conditions.
  • No side reactions
  • Robust catalytic process
  • Lack of functional group interference
  • A thermally and hydrolytically stable triazole connection
  • Unprecedented level of selectivity, reliability, and scope for syntheses which require covalent linkage between biochemical species.
Modifications Available at IDT:
Modification Name Used for modifying oligos with
5', Int, 3' Azide (NHS Ester) 5’, 3’, or internal azide functional group
5' Hexynyl 5’ alkyne functional group
5', Int, 3' 5-Octadiynyl dU 5’, 3’, or internal alkyne functional group
5', Int Biotin (Azide) 5’ or internal biotin functional group
5', Int 6-FAM (Azide) 5’ or internal 6-FAM functional group
5', Int 5-TAMRA (Azide) 5’ or internal 5-TAMRA functional group

To order an alkyne or azide modified oligo:

Specify the nucleic-acid sequence along with the appropriate alkyne or azide modifications included in the sequence.

To order an oligo modified by a 1,2,3-triazole linkage of Biotin, 6-FAM, or 5-TAMRA :

Select the desired azide modification at the desired location within the nucleic-acid sequence. IDT will synthesize the oligo, perform the click chemistry reaction, and purify the product.

References

  1. Rostovtsev, V.V., et al., A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew Chem Int Ed Engl, 2002. 41(14): p. 2596-9.
  2. Moses, J.E. and A.D. Moorhouse, The growing applications of click chemistry. Chem Soc Rev, 2007. 36(8): p. 1249-62.

Click-Chemistry enabled, modified oligos are manufactured and sold under license from Baseclick GmbH, using Base-click's proprietary Click Chemistry. All such modified products are sold by IDT for the end-user's internal research purposes only. See www.baseclick.org for further details.

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