Click Chemistry Reagents – TBTA & More


Click chemistry is a newer approach to the synthesis of drug-like molecules that can accelerate the drug discovery process. Sharpless, et al. defined what makes a click reaction as one that is wide in scope and easy to perform, uses only readily available reagents, and is insensitive to oxygen and water. Of the reactions comprising the click universe, the “perfect” example is the Huisgen 1,3-dipolar cycloaddition of alkynes to azides to form 1,4-disubstituted-1,2,3-triazoles (Scheme 1).1-4

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).1-4 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 disproportionation, while enhancing its catalytic activity.5 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.5

Product

Size

Catalog #

"TBTA, Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] amine" NEW

500 mg

63360-500

"TBTA, Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl] amine" NEW

50 mg

63360-50

For use as a tool in the drug discovery process, AnaSpec is pleased to announce the availability of TBTA, and also the availability of the following click chemistry reagents.


Amino acids with an azido group

Fmoc-azidohomoalanine Cat# 63670

Boc-azidolysine, Boc-Lys(N3)-OH, Cat# 53100-B025 & 53100-B1

Boc-azidohomoalanine, Boc-HomoAla-OH, Cat# 64167

Fmoc-azidolysine, Fmoc-Lys(N3)-OH,

Cat# 53100-F025/F1

Azidohomoalanine Cat#63669




Amino acids with an alkyn group

2-amino-3-mercapto-N-(prop-2-ynyl)propionamide Cat# 64168

Fmoc-L-propargylglycine, Cat# 26264-F1/F5
CAS# 198561-07-8

Boc-L-propargylglycine, Cat# 26264-B1/B5
CAS# 63039-48-5

Fmoc-D-propargylglycine, Cat#26265-F1/F5
"Fmoc-D-Pra-OH, CAS# 220497-98-3

Boc-D-propargylglycine•DCHA, Cat#26265-B1/B5
CAS# 63039-47-4



References:

  1. Kolb, HC. And KB. Sharpless Drug Discovery Today 8, 1128 (2003).
  2. Kolb, HC. et al. Angew. Chem. Int. Ed. 40, 2004 (2001).
  3. Rostovtsev, VV. and KB. Sharpless Angew. Chem. Int. Ed. 41, 2596 (2002).
  4. Tornøe, CW. et al. J. Org. Chem. 67, 3057 (2002).
  5. Chan, TR. et al. Org. Lett. 6, 2853 (2004).