Alkyne-containing Reagents for Cu(I)-catalyzed Click Reactions

One of the most popular reactions within the click chemistry paradigm is the Cu(I)-catalyzed 1,3-dipolar Huisgen cycloaddition of alkynes and azides, using a Copper (Cu) catalyst at room temperature. This reaction proceeds with great efficiency and selectivity in aqueous media and yields a triazole moiety.
 
Click Chemistry Reaction Scheme 1 (aryl-azide)

 
In contrast to many crosslinking methods used in biological research, this reaction depends upon a pair of unique groups with very specific reactivity to one another. Since neither alkynes nor azides occur in cells, they react only with each other in biological media, resulting in minimal background or side reactions. The Cu(I)-catalyzed azide-alkyne ligation reaction has endless applications where toxicity is irrelevant, from probing enzyme activity, visualizing biomolecules in fixed cells to detection of DNA synthesis in proliferating cells and to selective attachment of flourophores to viruses. However, in many biological applications the presence of Cu(I) is unacceptable due to its toxicity.
 

Assay Kits

Easy to use kits containing all reagents required for the detection of cell proliferation via labeling of incorporated EdU by Cu-catalyzed azide-alkyne cycloaddition reaction
 

Click Chemistry Kits

Easy to use kits containing all reagents required for labeling of alkyne-modified oligonucleotides or alkyne-modified PCR products with marker azides of your choice via Cu-catalyzed azide-alkyne cycloaddition reaction
 

Alkyne-containing Nucleosides

Nucleosides such as EdU (5-Ethynyl-2'-deoxyuridine) containing reactive triple bonds, allowing attachment of reporter groups by click chemistry techniques
 

Alkyne-containing Nucleotides

Nucleotides used to generate DNA containing reactive triple bonds, allowing attachment of reporter groups by click chemistry techniques
 

Alkyne-containing CEPs

Cyanoethyl-N,N-diisopropyl Phosphoramidites (CEPs) used to synthesize oligonucleotides by automated standard protocols. The resulting oligonucleotides contain triple bonds for attachment of azide-containing reporter groups.
 

Alkyne-containing CPGs

CPGs (Controlled Pore Glasses) for the synthesis of oligonucleotides by automated standard protocols. The resulting oligonucleotides contain triple bonds for attachment of azide-containing reporter groups.
 

Alkyne-containing Fluorescent Dyes

Fluorescent dyes containing reactive triple bonds for attachment to Azide-labeled molecules by click reactions
 

Alkyne-containing Biotinylation Reagents

Alkyne-containing reagents for the introduction of Biotin moieties
 

Alkyne-containing Spacers

Spacer building blocks containing reactive triple bonds
 

Alkyne-containing Chemical Modification Reagents

Alkyne-containing reagents for introduction of functional groups, such as amines or NHS esters
 

Auxiliary Reagents

Catalysts, ligands and solvents for click reactions
 


Selected references:
[1] Borsenberger et al. (2009) Diene-modified nucleotides for the Diels–Alder-mediated functional tagging of DNA. Nucleic Acids Research 37 (5):1477.
[2] Gramlich et al. (2008) Click–Click–Click: Single to Triple Modification of DNA. Angew. Chem. Int. Ed. 47:3442.
[3] Gramlich et al. (2008) Postsynthetic DNA Modification through the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction. Angew. Chem. Int. Ed. 47:8350.
[4] Seela et al. (2008) Modification of DNA with Octadiynyl Side Chains: Synthesis, Base Pairing, and Formation of Fluorescent Coumarin Dye Conjugates of Four Nucleobases by the Alkyne-Azide "Click" Reaction. Bioconjugate Chem. 19:211.
[5] Hammond et al. (2007) DNA Photography: An Ultrasensitive DNA-Detection Method Basedon Photographic Techniques. Angew. Chem. Int. Ed. 46:4184.
[6] Gierlich et al. (2007) Synthesis of Highly Modified DNA by a Combination of PCR with Alkyne-Bearing Triphosphates and Click Chemistry. Chem. Eur. J. 13:9486.
[7] Evans (2007) The Rise of Azide–Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification". Australian Journal of Chemistry 60 (6):384.
[8] Burley et al. (2006) Direct DNA Metallization. J. Am. Chem. Soc. 128:1398.
[9] Tornoe et al. (2002) Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides. Journal of Organic Chemistry 67 (9):3057.
[10] Kolb et al. (2001) Click chemistry: diverse chemical function from a few good reactions. Angew. Chem. Int. Ed. 40 (11):2004.
[11] Guida et al. (1996) Med. Res. Rev. p3.

For a comprehensive list of click chemistry related references, please see http://www.scripps.edu/chem/sharpless/click.html