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Electron transfer vs. proton transfer within radical-cation clusters of guanosine and deoxyguanosine with substituted naphthalenes and sinapinic acid

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Journal of the American Society for Mass Spectrometry

Abstract

Guanosine (G) and deoxyguanosine (dG) radical cations can be generated in the gas phase by single electron transfer (SET) within nucleoside-dimethoxynaphthalenes (1–2) electron-bound heterodimers produced by fast atom bombardment in a four sector mass spectrometer. The nucleobase guanine is much more easily oxidized when it is linked to a ribose moiety. The radical cation dimers formed by G and dG with sinapinic acid behave as proton-bound heterodimers. The experiments mimic to some extent the migration of radical sites within stacking bases which causes DNA damaging through depurination processes.

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References

  1. Colson, A. O.; Sevilla, M. D. Int. J. Radiation Biol. 1995, 67, 627.

    Article  CAS  Google Scholar 

  2. Holmlin, R. E.; Dandliker, P. J.; Barton, J. K. Angew. Chem. Int. Ed. Engl. 1997, 36, 2714.

    Article  Google Scholar 

  3. Hall, D. B.; Holmlin, R. E.; Barton, J. K. Nature 1996, 382, 731.

    Article  CAS  Google Scholar 

  4. Bron, A. M.; Harriman, A. J. J. Am. Chem. Soc. 1994, 116, 10383.

    Article  Google Scholar 

  5. Arkin, M. R.; Stemp, E. D.; Pulver, S. C.; Barton, J. K. Chem. Biol. 1997, 4, 389.

    Article  CAS  Google Scholar 

  6. Kanai, K.; Saito, I.; Kawashima, E.; Ishido, Y. Tetrahedron Lett. 1999, 40, 2589.

    Article  Google Scholar 

  7. Barber, M.; Bordoli, R. S.; Sedgwick, R. D.; Tyler, A. N. J. Chem. Soc. Chem. Commun. 1981, 325.

  8. Laramèe, J. A.; Arbogats, B.; Deinzer, M. L. Anal. Chem. 1989, 61, 2154.

    Article  Google Scholar 

  9. Liguori, A.; Marino, T.; Napoli, A.; Sindona, G.; Turbante, D. J. Mass Spectrom. Rapid Commun. Mass Spectrom. 1995, S47.

  10. Crain, P. F. Mass Spectrom. Rev. 1990, 8, 505.

    Article  Google Scholar 

  11. Sindona, G. In Mass Spectrometry in the Biological Sciences: A tutorial; Gross, M. L., Ed.; Kluwer: Dordrecht, 1992; pp 383–405.

    Google Scholar 

  12. De Pauw, E. Anal. Chem. 1983, 55, 2196.

    Article  Google Scholar 

  13. Athanassopoulos, C.; Papaioannou, D.; Napoli, A.; Siciliano, C.; Sindona, G. J. Mass Spectrom. 1995, 30, 1284.

    Article  CAS  Google Scholar 

  14. Cooks, R. G.; Wong, P. S. H. Acc. Chem. Res. 1998, 31, 379.

    Article  CAS  Google Scholar 

  15. Wong, P. S. H.; Ma, S.; Cooks, R. G. Anal. Chem. 1996, 68, 4254.

    Article  CAS  Google Scholar 

  16. Hwang, C. T.; Stumpf, C. L.; Yu, Y.-Q.; Kentamäa, H. I. Int. J. Mass Spectrom. 1999, 182/183, 253.

    Article  Google Scholar 

  17. Whitehill, A. B.; George, M.; Gross, M. L. J. Am. Chem. Soc. 1996, 118, 853.

    Article  CAS  Google Scholar 

  18. Kochi, J. K. In Advances in Physical Organic Chemistry; Bethell, D., Ed.; Academic: San Diego, 1994; Vol. 29, pp 234.

    Google Scholar 

  19. Cottrell, P. T.; Mann, C. K. J. Am. Chem. Soc. 1971, 93, 3579.

    Article  Google Scholar 

  20. Hamad, T.; Nishida, A.; Matsumoto, Y.; Yonemitsu, O. J. Am. Chem. Soc. 1980, 102, 3977.

    Google Scholar 

  21. Dervan, P. B.; Becker, M. M. J. Am. Chem. Soc. 1978, 100, 1968.

    Article  CAS  Google Scholar 

  22. Greco, F.; Liguori, A.; Sindona, G.; Uccella, N. J. Am. Chem. Soc. 1990, 112, 9092.

    Article  CAS  Google Scholar 

  23. Liguori, A.; Napoli, A.; Sindona, G. Rapid. Commun. Mass Spectrom. 1994, 8, 89.

    Article  CAS  Google Scholar 

  24. Castonguay, J.; Rossi, A.; Richer, J. C.; Rousseau, Y. Org. Mass Spectrom. 1972, 6, 1225.

    Article  CAS  Google Scholar 

  25. Busch, K. L.; Glish, G. L.; McLuckey, S. A. Mass Spectrometry/Mass Spectrometry. Techniques and Applications of Tandem Mass Spectrometry; VCH: New York, 1988.

    Google Scholar 

  26. Land, C. M.; Kinsel, G. R. J. Am. Soc. Mass Spectrom. 1998, 9, 1060.

    Article  CAS  Google Scholar 

  27. Klasinc, L.; Kovac, B.; Gusten, H. Pure Appl. Chem. 1983, 55, 289.

    Article  CAS  Google Scholar 

  28. Yoon, K. B.; Kochi, J. K. J. Phys. Chem. 1991, 95, 3780.

    Article  CAS  Google Scholar 

  29. Maurer, A. H.; Roberts, B. G.; Zweig, A. J. Org. Chem. 1967, 32, 1322.

    Article  Google Scholar 

  30. Anderson, G. M. III; Kollman, P. A.; Domelsmith, L. N.; Houk, K. N. J. Am. Chem. Soc. 1979, 101, 2344.

    Article  CAS  Google Scholar 

  31. Schaldach, B. Int. J. Mass Spectrom. Ion Processes 1984, 56, 237.

    Article  CAS  Google Scholar 

  32. Liguori, A.; Napoli, A.; Sindona, G. J. Mass Spectrom. 2000, 34, 139.

    Article  Google Scholar 

  33. Burrows, J. C.; Muller, J. G. Chem. Rev. 1998, 98, 1109.

    Article  CAS  Google Scholar 

  34. Rodgers, M. T.; Campbell, S.; Marzluff, E. M.; Beauchamp, J. L. Int. J. Mass Spectrom. Ion Processes 1993, 128, 1–23.

    Article  Google Scholar 

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Correspondence to Giovanni Sindona.

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Liguori, A., Napoli, A. & Sindona, G. Electron transfer vs. proton transfer within radical-cation clusters of guanosine and deoxyguanosine with substituted naphthalenes and sinapinic acid. J Am Soc Mass Spectrom 12, 176–179 (2001). https://doi.org/10.1016/S1044-0305(00)00215-4

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  • DOI: https://doi.org/10.1016/S1044-0305(00)00215-4

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