posted 09-22-2008 11:43 PM            

Copper (I) species are powerful catalysts for the formation of 1,2,3-triazoles from azides and alkynes. The general thermodynamic instability of Cu(I) however, results in easy oxidation to Cu(II) and/or disproportionation to Cu(0) and Cu(II).1 TBTA, Tris-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine, also known as tris-(benzyltriazolylmethyl)amine, is a stabilizing ligand for Cu(I) developed by Tim Chan in Sharpless’ lab. TBTA protects Cu(I) from oxidation and dispropotionation, while enhancing its catalytic activity.1-2 A C3-symmetric derivative, TBTS is an extremely useful ligand for azide-alkyne cycloaddition with ~106 fold of rate acceleration. Its tetradentate binding ability is able to completely envelop the Cu(I) center, leaving no free binding sites available for potential destabilizing interaction., Reactions are typically carried out with 1-2 mol % Cu(I) and TBTA without having to exclude oxygen and water.3

For use as a tool in the drug discovery process, AnaSpec carries TBTA, the click chemistry reagent used in Cu(I)TBTA-catalyzed azide-alkyne cycloaddition. TBTA, with a MW of 530.6, is supplied in powder form at 97% purity.

References:
1. Chan, TR. et al. Org. Lett. 6, 2853 (2004).
2. Sharpless, KB. and MG. Finn, J. Am. Chem. Soc. 2003, 125, 3192.
3. Kolb, HC. and KB. Sharpless, Drug Discovery Today, 2003, 8, 1128.

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