View Shopping Cart   Checkout   Order Catalog  

BA 0308
Product Information Molecular Structure

5-Octadiynyl-dU CEP

Notes: Useful for the installation of an alkyne-bearing nucleoside into an oligonucleotide. The flexible tether allows for efficient elaboration via Click chemistry.

Description: 

An attractive strategy for nucleic acid conjugation involves the Cu(I)-catalyzed click reaction between terminal alkynes and azides. While 5-Ethynyl-dU in oligonucleotides has been reported to undergo the click reaction,1 the short rigid nature of the alkyne group severely limits its application for this purpose. 5-Octadiynyl-dU CEP (BA 0308)1-5 is a much superior reagent for the installation of an alkyne-bearing nucleoside into an oligonucleotide when click reactions are contemplated. The terminal alkyne is more flexible and extends farther away from thr pyrimidine ring, thereby allowing more efficient ligation via click chemistry, even when multiple ligations to a single oligo are desired. Interestingly, the 5-Octadiynyl-dU modification gives a slight stabilization of DNA duplexes, much like the well-known effect of propynyl-dU modification.3

For more information on this product and its use, download a Product Information Sheet here.

For a complete listing of our reagents for click chemistry, please see our Click-matesTM Collection page.

(1) Gierlich, J.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. M.; Carell, T. Org. Lett. 2006, 8, 3639-3642.

(2) Seela, F.; Sirivolu, V. R. Chem. Biodiversity 2006, 3, 509-514. Gierlich, J.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. M.; Carell, T. Org. Lett. 2006, 8, 3639-3642.

(3) Seela, F.; Sirivolu, V. R. Helv. Chim. Acta 2007, 90, 535-552.

(4) Hammond, D. M.; Manetto, A.; Gierlich, J.; Azov, V. A.; Gramlich, P. M. E.; Burley, G. A.; Maul, M.; Carell, T. Angew. Chem. Int. Ed. 2007, 46, 4184-4187.

(5) Rozkiewicz, D. I.; Gierlich, J.; Burley, G. A.; Gutsmiedl, K.; Carell, T.; Ravoo, B. J.; Reinhoudt, D. N. ChemBioChem 2007, 8, 1997-2002.

This compound is sold under license from baseclick GmbH, and the purchase of these products for use in applications relating to copper catalyzed azide-alkyne cycloaddition chemistry (“Click Chemistry”) includes a limited, nontransferable license to intellectual property owned by TSRI to use this product solely for internal non-commercial research activities and specifically excludes clinical, therapeutic, or diagnostic use in humans or animals. Information regarding a license for commercial use in Click Chemistry may be obtained directly from The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, CA 92037, or by contacting 858-784-8140 or click@scripps.edu.

5-Octadiynyl-dU CEP
Product Details Product Pricing

MF: C47H55N4O8P

MW: 834.94

CAS NO: 938186-76-6

Storage Conditions: -20 oC, dry

Purity≥95%

Availability: 

Stock maintained. Ships within 1-3 days.

Unit Weight Unit Price Quantity
100 µmol $255.00
0.25 g $550.00
 
View Shopping CartCheckout