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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)