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AnaSpec Introduces New Click Chemistry Reagents

 
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anaspec



Joined: 15 Aug 2006
Posts: 238
Location: 34801 Campus Drive, Fremont, CA 94555

PostPosted: Fri Aug 21, 2009 2:20 pm    Post subject: AnaSpec Introduces New Click Chemistry Reagents Reply with quote

San Jose, CA – August 21, 2009
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
For use as a tool in the drug discovery process, AnaSpec is pleased to announce the availability of TBTA and a number of additional click chemistry reagents.
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).

About AnaSpec

AnaSpec is a leading provider of integrated proteomics solutions to the world’s largest biotech, pharmaceutical, and academic research institutions. With a vision for innovation through synergy, AnaSpec focuses on three core technologies: peptides, detection reagents, and antibodies.

For more information visit www.anaspec.com

###
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Ping Yang
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34801 Campus Drive
Fremont, CA 94555
1-800-452-5530 (Toll free)
1-510-791-9560 (Tel)
1-510-791-9572 (Fax)
ping@anaspec.com
www.anaspec.com
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