description

THPTA is a water soluble alternative to TBTA (RL-2010) and highly efficient catalyst or ligand for click chemistry in partially organic and particularly in completely aqueous reactions. The benefits of a completely aqueous reaction include the biological labeling of live cells or the labeling of proteins without the concern of denaturing secondary structures. THPTA complexes Cu(I) hence is blocking the bioavailability of Cu(I) and ameliorating the potential toxic effects while maintaining the catalytic effectiveness in click conjugations. Successful Click reactions with oligonucleotids can be found in many publications.

references

A coumarin derivative as a fluorogenic glycoproteomic probe for biological imaging; Lei Rong, Li-Han Liu, Si Chen, Han Cheng, Chang-Sheng Chen, Ze-Yong Li, Si-Yong Qina and

Xian-Zheng Zhang; Chem. Commun. 2014; 50: 667-669; DOI: 10.1039/C3CC47323F.

A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes; Vsevolod V. Rostovtsev, Luke G. Green, Valery V. Fokin, K.

Barry Sharpless; Angew. Chem. Int. Ed. Engl. 2002; 41(14): 2596-2599. DOI: 10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4.

Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides; Christian W Tornøe, Caspar

Christensen, Morten Peter Meldal; J. Org. Chem. 2002; 67(9): 3057-64. DOI: 10.1021/jo011148j.

Polytriazoles as copper(I)-stabilizing ligands in catalysis; Timothy R. Chan, Robert Hilgraf, K. Barry Sharpless, Valery V. Fokin; Org Lett. 2004; 6(17): 2853-2855. DOI:

10.1021/ol0493094.

Labeling Live Cells by Copper-Catalyzed Alkyne-Azide Click Chemistry; Hong, V.; Steinmetz, N.F.; Manchester, M.; Finn, M.G.; Bioconjugate Chem. 2010; 21: 1912-1916.

Click-Click-Click: Single to Triple Modification of DNA; Philipp M. E. Gramlich, Simon Warncke, Johannes Gierlich, Thomas Carell; Angew. Chem. Int. Ed. Engl. 2008; 47(18):

3442-3444; DOI: 10.1002/anie.200705664.

Site-selective modification of proteins for the synthesis of structurally defined multivalent scaffolds; L. M. Artner, L. Merkel, N. Bohlke, F. Beceren-Braun, C. Weise, J.

Dernedde, N. Budisa and C. P. R. Hackenberger; Chemical Communications 2012; 48: 522-524. doi:10.1039/c1cc16039g

Covalent Cell Surface Functionalization of Human Fetal Osteoblasts for Tissue Engineering; F. Borcard, A. Godinat, D. Staedler, H. Comas Blanco, A.-L. Dumont, C.

Chapuis-Bernasconi, C. Scaletta, L. A. Applegate, F. Krauss Juillerat, U. T. Gonzenbach, S. Gerber-Lemaire and L. Juillerat-Jeanneret; Bioconjugate Chemistry 2011; 22: 1422-1432.

doi:10.1021/bc200147m

Relative Performance of Alkynes in Copper-Catalyzed Azide-Alkyne Cycloaddition; A. A. Kislukhin, V. P. Hong, K. E. Breitenkamp and M. G. Finn; Bioconjugate Chemistry 2013; 24:

684-689. doi:10.1021/bc300672b

Efficient Synthesis of Linear Multifunctional Poly(ethylene glycol) by Copper(I)-Catalyzed Huisgen 1,3-Dipolar Cycloaddition; X.-M. Liu, A. Thakur and D. Wang; Biomacromolecules

2007; 8: 2653-2658. doi:10.1021/bm070430i

Ligand-Assisted, Copper(II) Acetate-Accelerated Azide-Alkyne Cycloaddition; H. A. Michaels and L. Zhu; Chemistry - An Asian Journal 2011; 6: 2825-2834. doi:10.1002/asia.201100426

Oligonucleotide and Polymer Functionalized Nanoparticles for Amplification-Free Detection of DNA; D. A. C. Thomson, E. H. L. Tee, N. T. D. Tran, M. J. Monteiro and M. A. Cooper;

Biomacromolecules 2012; 13: 1981-1989. doi:10.1021/bm300717f

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