Evidence for glycosidic bond rotation in a nucleobase peroxyl radical and its effect on tandem lesion formation

Journal of Organic Chemistry

Volumn 69, Issue 21, 2004, Pages 6974-6978

  Hong, In Seok ^a   Carter, K Nolan ^a   Greenberg, Marc M ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; DNA; RADIOLYSIS;

DIASTEREOMERS; REACTION PATHWAYS; REACTIVE INTERMEDIATES;

BIOPOLYMERS;

BIOPOLYMER; DEOXYURIDINE DERIVATIVE; NUCLEIC ACID BASE; PEROXY RADICAL;

AEROBIC CAPACITY; ARTICLE; CHEMICAL BOND; CONFORMATION; DIASTEREOISOMER; DNA DAMAGE; DNA PROBE; DNA STRUCTURE; RADIATION EXPOSURE; RADIOLYSIS; REACTION ANALYSIS;

DNA; DNA DAMAGE; FREE RADICALS; GLYCOSIDES; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; NUCLEOSIDES; PULSE RADIOLYSIS; STEREOISOMERISM;

EID: 5444220795     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0492158     Document Type: Article

References (36)

1. Cadet, J.; Douki, T.; Gasparutto, D.; Ravanat, J. L. Mutat. Res. 2003, 531, 5-23.
2. Bjelland, S.; Seeberg, E. Mutat. Res. 2003, 531, 37-80.
3. Dizdaroglu, M.; Jaruga, P.; Birincioglu, M.; Rodriguez, H. Free Radical Biol. Med. 2002, 32, 1102-1115.
4. Bellon, S.; Ravanat, J.-L.; Gasparutto, D.; Cadet, J. Chem. Res. Toxicol. 2002, 15, 598-606.
5. Douki, T.; ReynaudAngelin, A.; Cadet, J.; Sage, E. Biochemistry 2003, 42, 9221-9226.
6. Douki, T.; Riviere, J.; Cadet, J. Chem. Res. Toxicol. 2002, 15, 445-454.
7. Box, H. C.; Budzinski, E. E.; Dawidzik, J.; Patrzyc, H. B.; Freund, H. G. Radiat. Res. 2001, 156, 215-219.
8. Liu, Z.; Gao, Y.; Wang, Y. Nucleic Acids Res. 2003, 31, 5413-5424.
9. Zhang, Q.; Wang, Y. J. Am. Chem. Soc. 2003, 125, 12795-12802.
10. Tallman, K. A.; Greenberg, M. M. J. Am. Chem. Soc. 2001, 123, 5181-5187.
11. Lomax, M. E.; Gulston, M. K.; O'Neill, P. Radiat. Prot. Dosim. 2002, 99, 63-68.
12. Sutherland, B. M.; Georgakilas, A. G.; Bennett, P. V.; Laval, J.; Sutherland, J. C. Mutat. Res. 2003, 531, 93-107.
13. Kawai, K. S. I.; Sugiyama, H. J. Am. Chem. Soc. 1999, 121, 1391-1392.
14. Sugiyama, H.; Fujimoto, K.; Saito, I. Tetrahedron Lett. 1996, 37, 1805-1808.
15. Sugiyama, H. S., I. J. Am. Chem. Soc. 1990, 112, 6720-6721.
16. Cook, G. P.; Chen, T.; Koppisch, A. T.; Greenberg, M. M. Chem. Biol. 1999, 6, 451-459.
17. Cook, G. P.; Greenberg, M. M. J. Am. Chem. Soc. 1996, 118, 10025-10030.
18. Carter, K. N.; Greenberg, M. M. J. Am. Chem. Soc. 2003, 125, 13376-13378.
19. von Sonntag, C. The Chemical Basis of Radiation Biology; Taylor & Francis: London, 1987.
20. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1983.
21. Carter, K. N.; Greenberg, M. M. J. Org. Chem. 2003, 68, 4275-4280.
22. Miaskiewicz, K.; Miller, J.; Osman, R. Biochim. Biophys. Acta 1994, 1218, 283-291.
23. Miaskiewicz, K.; Miller, J.; Ornstein, R.; Osman, R. Biopolymers 1995, 35, 113-124.
24. Jones, G. D. D.; O'Neill, P. Int. J. Radiat. Biol 1990, 57, 1123-1139.
25. Schulte-Frohlinde, D.; Behrens, G.; Önal, A. Int. J. Radiat. Biol 1986, 50, 103-110.
26. Bothe, E.; Behrens, G.; Böhm, E.; Sethuram, B.; Schulte-Frohlinde, D. Int. J. Radiat. Biol 1986, 49, 57-66.
27. Hwang, J.-T.; Tallman, K. A.; Greenberg, M. M. Nucleic Acids Res. 1999, 27, 3805-3810.
28. Zheng, Y.; Sheppard, T. L. Chem. Res. Toxicol. 2004, 17, 197-207.
29. Hildenbrand, K.; Schulte-Frohlinde, D. Int. J. Radiat. Biol. 1997, 71, 377-385.
30. Chenier, J. H. B.; Furimsky, E.; Howard, J. A. Can. J. Chem. 1974, 52, 3682.
31. Iwai, S. Chem.-Eur. J. 2001, 7, 4343-4351.
32. Kung, H. C.; Bolton, P. H. J. Biol. Chem. 1997, 272, 9227-9236.
33. Guéron, M.; Leroy, J. Methods Enzymol. 1995, 261, 383-412.
34. Miller, H.; Fernandes, A. S.; Zaika, E.; McTigue, M. M.; Torres, M. C.; Wente, M.; Iden, C. R.; Grollman, A. P. Nucleic Acids Res. 2004, 32, 338-345.
35. Tan, J.; Geacintov, N. E.; Broyde, S. Chem. Res. Toxicol. 2000, 13, 811-822.
36. Katafuchi, A.; Nakano, T.; Masaoka, A.; Terato, H.; Iwai, S.; Hanaoka, F.; Ide, H. J. Biol. Chem. 2004, 279, 14464-14471.