THPTA: Ligand-accelerated Click Chemistry in Aqueous Solution

Published on 26/04/2016

Polytriazole ligands such as THPTA accelerate the copper-catalyzed azide-alkyne cycloaddition (CuAAC), or “Click”, reaction. Moreover, with the use of further additives, polytriazoles facilitate CuAAC even in live cells by significantly lowering the bioavailability of the copper catalyst.

Polytriazoles such as TBTA are efficient accelerating ligands for the copper-catalyzed azide-alkyne cycloaddition (CuAAC). THPTA is a water-soluble alternative of TBTA suitable for conjugation reactions under physiological conditions. Using THPTA in combination with ascorbate and aminoguanidine as copper-protective reagents, CuAAC can even be performed on live cells (Hong et al., Bioconj. Chem. 2010).

THPTA: Ligand-accelerated Click Chemistry in Aqueous Solution

References

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
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
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
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
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
Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry; V. Hong, N. F. Steinmetz, M. Manchester and M. G. Finn; Bioconjugate Chemistry 2010; 21: 1912-1916. doi:10.1021/bc100272z
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