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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:

 
  1. Reaction occurs in aqueous solution and at room temperature
  2. Stability toward H2O, O2, and most organic synthesis conditions.
  3. No side reactions
  4. Robust catalytic process
  5. Lack of functional group interference
  6. A thermally and hydrolytically stable triazole connection
  7. Unprecedented level of selectivity, reliability, and scope for syntheses which require covalent linkage between biochemical species.
 
Modifications Available at IDT:

Modification NameUsed for modifying oligos with
5', Int, 3' Azide (NHS Ester)5’, 3’, or internal azide functional group
5' Hexynyl5’ alkyne functional group
5', Int, 3' 5-Octadiynyl dU5’, 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.