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Water-soluble Ligand for Bioorthogonal Click Reactions
Tris(3-hydroxypropyltriazolylmethyl)amine (THPTA) is a water-soluble ligand, which is synthesized by the click reaction (= Hüisgen 1,3-dipolar cycloaddition reaction) using tripropargyl amine and 3-azido-1-propanol.1) In the presence of a copper ion, THPTA can be applied to Cu-catalyzed alkyne-azide cyclization (CuAAC), the typical bioorthogonal reaction with non-interferance in living systems. By forming a copper complex it will accelerate the CuAAC process.2) Therefore, CuAAC using THPTA is applicable to not only the modification of hydrophilic polymers3) and the bioconjugation of peptides containing an azido group,4) but also the rapid labeling of metabolically-incorporated azido or alkyne tags on living cell surfaces.5)
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References
- 1)Polytriazoles as Copper(I)-Stabilizing Ligands in Catalysis
- 2)Analysis and Optimization of Copper-Catalyzed Azide–Alkyne Cycloaddition for Bioconjugation
- 3)Stabilization of Virus-like Particles with Poly(2-oxazoline)s
- 4)Synthesis of Cyclic Peptide Disulfide–PHPMA Conjugates via Sequential Active Ester Aminolysis and CuAAC Coupling
- 5)a) Cellular Consequences of Copper Complexes used to Catalyze Bioorthogonal Click Reactions
- D. C. Kennedy, C. S. McKay, M. C. B. Legault, D. C. Danielson, J. A. Blake, A. F. Pegoraro, A. Stolow, Z. Mester, J. P. Pezacki, J. Am. Chem. Soc. 2011, 133, 17993.
- b) Labeling Live Cells by Copper-Catalyzed Alkyne−Azide Click Chemistry
- V. Hong, N. F. Steinmetz, M. Manchester, M. G. Finn, Bioconjugate Chem. 2010, 21, 1912.
- D. C. Kennedy, C. S. McKay, M. C. B. Legault, D. C. Danielson, J. A. Blake, A. F. Pegoraro, A. Stolow, Z. Mester, J. P. Pezacki, J. Am. Chem. Soc. 2011, 133, 17993.