Oxidation of 5-hydroxy-2′-deoxyuridine into isodialuric acid, dialuric acid, and hydantoin products

Journal of the American Chemical Society

Volumn 126, Issue 21, 2004, Pages 6548-6549

  Rivière, Johann ^a   Bergeron, François ^a   Tremblay, Sébastien ^a   Gasparutto, Didier ^b   Cadet, Jean ^b   Wagner, J Richard ^a  

^a UNIVERSITY OF SHERBROOKE   (Canada)

^b CEA GRENOBLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

5 HYDROXYDEOXYURIDINE; DIALURIC ACID; GUANINE DERIVATIVE; HYDANTOIN DERIVATIVE; ISODIALURIC ACID; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ARTICLE; DNA DAMAGE; DNA STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZING RADIATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; OXIDATION; PHOTOSENSITIZATION; REACTION ANALYSIS; ULTRAVIOLET RADIATION;

BARBITURATES; DEOXYURIDINE; HYDANTOINS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; URACIL;

EID: 2542609803     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049438f     Document Type: Article

References (26)

1. (a) Cadet, J.; Delatour, T.; Douki, T.; Gasparutto, D.; Pouget, J. P.; Ravanat, J. L.; Sauvaigo, S. Mutat. Res. 1999, 424, 9-21.
2. (b) Wallace, S. S. Free Radical Biol. Med. 2002, 33, 1-14.
3. (a) Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617-618.
4. (b) Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063-7068.
5. (a) Douki, T.; Cadet, J. Int. J. Radiat. Biol. 1999, 75, 571-581.
6. (b) Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109-1151.
7. (a) Ravanat, J. L.; Saint-Pierre, C.; Cadet, J. J. Am. Chem. Soc. 2003, 125, 2030-2031.
8. (b) Duarte, J. V.; Gasparutto, D.; Yamaguchi, L. F.; Ravanat, J. L.; Martinez, G. R.; Medeiros, M. H. G.; Di Mascio, P.; Cadet, J. J. Am. Chem. Soc. 2000, 122, 12622-12628.
9. (c) Luo, W. C.; Muller, J. G.; Rachlin, E. M.; Burrows, C. J. Org. Lett. 2000, 2, 613-616.
10. (d) Tretyakova, N. Y.; Niles, J. C.; Burney, S.; Wishnok, J. S.; Tannenbaum, S. R. Chem. Res. Toxicol. 1999, 12, 459-466.
11. (a) Wagner, J. R.; Decarroz, C.; Berger, M.; Cadet, J. J. Am. Chem. Soc. 1999, 121, 4101-4110.
12. (b) Bienvenu, C.; Wagner, J. R.; Cadet, J. J. Am. Chem. Soc. 1996, 118, 11406-11411.
13. (c) Girault, I.; Fort, S.; Molko, D.; Cadet, J. Free Radical Res. 1997, 26, 257-266.
14. (d) Hayatsu, H. J. Biochem. 1996, 119, 391-395.
15. Wagner, J. R.; Hu, C. C.; Ames, B. N. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3380-3384.
16. (a) Fujimoto, J.; Tran, L.; Sowers, L. C. Chem. Res. Toxicol. 1997, 10, 1254-8.
17. (b) Wolfe, J. L.; Kawate, T.; Sarracino, D. A.; Zillmann, M.; Olson, J.; Stanton, V. P.; Verdine, G. L. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 11073-11078.
18. (c) Yanagawa, H.; Ogawa, Y.; Ueno, M. J. Biol. Chem. 1992, 267, 13320-6.
19. (a) Schuchmann, M. N.; von Sonntag, C. J. Chem. Soc., Perkin Trans. 2 1983, 1525-1531.
20. 1H NMR analyses suggest that isodialuric acid is attached to an α-pranosyl moiety because of the chemical shift of H1′ (5.5 ppm) and H4′ (<4 ppm) and large coupling between H1′-H2′ (9.7 Hz).
21. (a) Bienvenu, C.; Cadet, J. J. Org. Chem. 1996, 61, 2632-2637.
22. (b) Wagner, J. R.; van Lier, J. E.; Berger, M.; Cadet, J. J. Am. Chem. Soc. 1994, 116, 2235-2242.
23. (c) Harayama, T.; Yanada, R.; Iio, K.; Yoneda, F. Nucleic Acids Symp. Ser. 1986, 17, 25-82.
24. (d) Ryang, H. S.; Wang, S. Y. J. Org. Chem. 1979, 44, 1191-1192.
25. (a) Feig, D. I.; Sowers, L. C.; Loeb, L. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6609-6613.
26. (b) Kreutzer, D. A.; Essigmann, J. M. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 3578-3582.