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BA 0382
Product Information Molecular Structure

(5'S)-8,5'-Cyclodeoxyguanosine (THP) CEP

Notes: This phosphoramidite is used for standard 3’ to 5’ oligonucleotide synthesis.

Description: 

The naturally occurring nucleosides, cyclo-dG and cyclo-dA are bridged cyclonucleosides that result from oxidative free radical damage to DNA. This specialized “tandem lesion” encompasses damage to both the sugar and the base moiety of the same purine nucleoside. This oxidative damage plays a significant role in mutagenesis, carcinogenesis and aging.1 Both of the bulky 8,5’-Cyclodeoxyadenosine (cyclo-dA) and the 8,5’-Cyclodeoxyguanosine (cyclo-dG) lesions have been shown to be present in human cells.1,2 Cyclo-dA and Cyclo-dG are both strong blockers of gene expression in CHO and human cells. These lesions can be repaired via nucleoside excision repair mechanisms, but not by base excision repair mechanisms.3 Structural investigations have shown that when incorporated into DNA, cyclo-dG stacks in the DNA duplex, retains Watson-Crick hydrogen bonding with dC, but significantly perturbs the helix structure near the lesion.4

Both cyclo- dA and cyclo-dG are valuable tools for investigations into DNA damage and repair. We offer the traditionally DMT protected cyclo-dA CEP (BA 0329), but the difficulties encountered when developing a practical synthesis for a cyclo-dG phosphoramidite that would be applicable to automated DNA synthesis led us away from the conventional 5’-DMT protection. A better alternative, which dramatically increases the overall yield of the synthesis, is to utilize a 5’-tetrahydropyranyl (THP) protecting group.

For additional information, download a Product Information Sheet.

References

1. a) Jaruga, P.; Dizdaroglu, M. DNA Repair, 2008, 7, 1413-1425. b) Cooke, M. S.; Evans, M. D.; Dizdaroglu, M.; Lunec, J. The FASEB Journal, 2003, 17, 1195-1214.

2. Dizdaroglu, M.; Dirksen, M.L.; Jiang, H.X.; Robbins, J.H. J. Biochem. 1987, 241, 929-932.

3. a) Brooks, P.J.; Wise, D.S.; Berry, D.A.; Kosmoski, J.V.; Smerdon, M.J.; Somers, R.L.; Mackie, H.; Spoonde, A.Y.; Ackerman, E.J.; Coleman, K.; Tarone, R.E.; Robbins, J.H. J. Biol. Chem. 2000, 275 , 22355-22362. b) Swanson, A. L.; Wang, J.; Wang, Y. Chem. Res. Toxicol. 2012, 25, 1682-1691. c) Pande, P.; Das, R.S.; Sheppard, C.; Kow, Y.W.; Basu, A.K. DNA Repair, 2012, 11, 926-931.

4. Huang, H.; Das, R.S.; Basu, A.K.; Stone, M.P. J. Am. Chem. Soc. 2011, 133, 20357-20368.

(5'<em>S</em>)-8,5'-Cyclodeoxyguanosine (THP) CEP
Product Details Product Pricing

MF: C28H42N7O7P

MW: 619.65

CAS NO: None Assigned

Storage Conditions: Dry, -20 °C

Purity≥95%

Availability: 

Stock maintained. Ships within 1-3 days.

Alternate Name: 

Cyclo dG CEP
Unit Weight Unit Price Quantity
50 µmol $1,250.00
 
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