Fate of the C-1′ peroxyl radical in the 2′-deoxyuridine system

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Chryssostomos Chatgilialoglu and Thanasis Gimisis


Abstract

The mechanism of 2-deoxyribonolactone formation from the reaction of photogenerated 2′-deoxyuridin-1′-yl radical with molecular oxygen in water has been investigated.


References

  1. DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases, ed. B. Meunier, Kluwer, Dordrecht, 1996 Search PubMedfor a review, see G. Pratviel, J. Bernadou and B. Meunier, Angew. Chem., Int. Ed. Engl., 1995, 34, 746 Search PubMed.
  2. For a recent review, see C. Chatgilialoglu and T. Gimisis, in Free Radicals in Biology and Environment, ed. F. Minisci, Kluwer, Dordrecht, 1997, pp. 281–292 Search PubMed.
  3. For some recent work, see X. Zeng, Z. Xi, L. S. Kappen, W. Tan and I. H. Goldberg, Biochemistry, 1995, 34, 12 435 Search PubMed; Y.-J. Xu, Z. Xi, Y.-S. Zhen and I. H. Goldberg, Biochemistry, 1995, 34, 12 451 CrossRef CAS; M. Pitié, J. Bernadou and B. Meunier, J. Am. Chem. Soc., 1995, 117, 2935 CrossRef CAS; H. Sugiyama, K. Fujimoto and I. Saito, J. Am. Chem. Soc., 1995, 117, 2945 CrossRef CAS; H. Sugiyama, K. Fujimoto, I. Saito, E. Kawashima, T. Sekine and Y. Ishido, Tetrahedron Lett., 1996, 37, 1805 CrossRef CAS; G. P. Cook and M. M. Greenberg, J. Am. Chem. Soc., 1996, 118, 10 025 CrossRef CAS; T. Melvin, S. W. Botchway, A. W. Parker and P. O'Neil, J. Am. Chem. Soc., 1996, 118, 10 031 CrossRef CAS; M. M. Meijler, O. Zelenko and A. S. Sigman, J. Am. Chem. Soc., 1997, 119, 1135 CrossRef CAS; H. Sugiyama, K. Fujimoto and I. Saito, Tetrahedron Lett., 1997, 38, 8057 CrossRef CAS; O. Zelenko, J. Gallagher and A. S. Sigman, Angew. Chem., Int. Ed. Engl., 1997, 36, 2776 CrossRef CAS.
  4. T. Gimisis and C. Chatgilialoglu, J. Org. Chem., 1996, 61, 1908 CrossRef CAS; T. Gimisis, C. Castellari and C. Chatgilialoglu, Chem. Commun., 1997, 2089 RSC.
  5. I. H. Goldberg, Acc. Chem. Res., 1991, 24, 191 CrossRef CAS; B. K. Goodman and M. M. Greenberg, J. Org. Chem., 1996, 61, 2 CrossRef CAS.
  6. E. G. Hole, W. H. Nelson, E. Sagstuen and D. M. Close, Radiat. Res., 1992, 129, 119 CAS; D. M. Close, W. H. Nelson, E. Sagstuen and E. O. Hole, Radiat. Res., 1994, 137, 300 CAS; K. Miaskiewicz and R. Osman, J. Am. Chem. Soc., 1994, 116, 232 CrossRef CAS; A.-O. Colson and M. D. Sevilla, J. Phys. Chem., 1995, 99, 3867 CrossRef CAS.
  7. C. Chatgilialoglu, T. Gimisis, M. Guerra, C. Ferreri, C. J. Emanuel, J. H. Horner, M. Newcomb, M. Lucarini and G. F. Pedulli, Tetrahedron Lett., in the press Search PubMed.
  8. T. Gimisis, G. Ialongo, M. Zamboni and C. Chatgilialoglu, Tetrahedron Lett., 1995, 36, 6781 CrossRef CAS; T. Gimisis, G. Ialongo and C. Chatgilialoglu, Tetrahedron, 1998, 54, 573 CrossRef CAS.
  9. M. M. Greenberg, D. J. Yoo and B. K. Goodman, Nucleosides Nucleotides, 1997, 16, 33 CAS.
  10. A. Holy, Nucleic Acids Res., 1974, 1, 289 CAS.
  11. K. Haraguchi, Y. Itoh, H. Tanaka, K. Yamaguchi and T. Miyasaka, Tetrahedron Lett., 1993, 34, 6913 CrossRef CAS; Y. Itoh, K. Haraguchi, H. Tanaka, E. Gen and T. Miyasaka, J. Org. Chem., 1995, 60, 656 CrossRef CAS.
  12. C. Chatgilialoglu, Acc. Chem. Res., 1992, 25, 118; C. Chatgilialoglu, Chem Rev., 1995, 95, 1229 CrossRef CAS.
  13. The reduction using Bu3SnH was reported to give 77% yield, see Y. Yoshimura, F. Kano, S. Miyazaki, N. Ashida, S. Sakata, K. Haraguchi, Y. Itoh, H. Tanaka and T. Miyasaka, Nucleosides Nucleotides, 1996, 15, 305 Search PubMed.
  14. For compounds 2 and 7, see F. J. Lopez-Herrera, M. Valpuesta-Fernandez and S. Garcia-Claros, Tetrahedron, 1990, 46, 7165 Search PubMed; A. P. Kozikowski and A. K. Ghosh, J. Org. Chem., 1984, 49, 2762 CrossRef CAS.
  15. (a) C. von Sonntag and H.-P. Schuchmann, Angew. Chem., Int. Ed. Engl., 1991, 30, 1229 CrossRef; (b) K. U. Ingold, T. Paul, M. J. Young and L. Doiron, J. Am. Chem. Soc., 1997, 119, 12 364 CrossRef CAS.
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