Self-assembling of cytosine nucleoside into triply-bound dimers in acid media. A comprehensive evaluation of proton-bound pyrimidine nucleosides by electrospray tandem mass spectrometry, X-rays diffractometry, and theoretical calculations

Journal of the American Society for Mass Spectrometry

Volumn 15, Issue 2, 2004, Pages 268-279

  Armentano, Donatella ^a   De Munno, Giovanni ^a   Di Donna, Leonardo ^a   Sindona, Giovanni ^a   Giorgi, Gianluca ^b   Salvini, Laura ^b  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERS; HYDROGEN BONDS; MONOMERS; PROTONS; SELF ASSEMBLY; X RAY DIFFRACTION ANALYSIS;

ELECTROSPRAYING; SUPERMOLECULES;

MASS SPECTROMETRY;

CYTOSINE; DIMER; NUCLEIC ACID BASE; NUCLEOSIDE; PYRIMIDINE; THYMINE; URACIL;

MASS SPECTROMETRY;

ARTICLE; CALCULATION; CRYSTALLOGRAPHY; DISSOCIATION; ELECTROSPRAY MASS SPECTROMETRY; GAS ANALYSIS; HYDROGEN BOND; KINETICS; MOLECULAR INTERACTION; PROTON TRANSPORT; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY; THEORY; X RAY DIFFRACTION;

EID: 0842310449     PISSN: 10440305     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jasms.2003.10.017     Document Type: Article

References (50)

1. Saenger W. Principles of Nucleic Acid Structure. 1984;Springer-Verlag, New York, NY.
2. Eckstein F., Lilley D.M.J. Nucleic Acids and Molecular Biology. 1990;2 Springer-Verlag, Berlin and Heidelberg.
3. Frank-Kamenetskii M.D., Mirkin S.M. Annu. Rev. Biochem. 64:1995;65.
4. Soyfer V.N., Potaman V.N. Triple-Helical Nucleic Acid. 1996;Springer-Verlag, New York, NY.
5. Chubb J.M., Hogan M.E. Trends Biotechnol. 10:1992;132.
6. Gee J.E., Miller D.M. Am. J. Med. Sci. 304:1992;366.
7. Hélène C. Anti-cancer Drug Des. 6:1991;569.
8. Wells R.D. J. Biol. Chem. 271:1996;2875.
9. Mitas M. Nucleic Acids Res. 25:1997;2245.
10. Richards R.I., Sutherland G.R. Cell. 70:1992;709.
11. Sinden R.R., Wells R.D. Curr. Opin. Biotechnol. 3:1992;612.
12. Pearson C.E., Sinden R.R. Curr. Opin. Struct. Biol. 8:1998;321.
13. Ashley C.T. Jr, Warren S.T. Annu. Rev. Genet. 29:1995;703.
14. de los Santos C., Rosen M., Patel D. Biochemistry. 28:1989;7282.
15. Rajagopal P., Feigon J. Nature. 339:1989;637.
16. Rajagopal P., Feigon J. Biochemistry. 28:1989;7859.
17. Weiner A.M. Cell. 52:1988;155.
18. Sijbesma R.P., Meijer E.W. Chem. Commun. 2003;5.
19. Sindona G., Uccella N., Weclawek K. J. Chem. Res. Suppl. 1982;184.
20. Panico M., Sindona G., Uccella N. J. Am. Chem. Soc. 105:1983;5607.
21. Beckey H.D., Levsen K., Roellgen F.W., Schulten H.R. Surf. Sci. 70:1978;325.
22. Fenn J.B., Mann M., Meng C.K., Whitehouse C.M. Science. 246:1989;64.
23. Koch K.J., Aggerholm T., Nanita S.C., Cooks R.G. J. Mass Spectrom. 37:2002;676.
24. Cooks R.G., Patrick J.S., Kotiaho T., McLuckey S.A. Mass Spectrom. Rev. 13:1994;287.
25. Greco F., Liguori A., Sindona G., Uccella N. J. Am. Chem. Soc. 112:1990;9092.
26. Liguori A., Napoli A., Sindona G. Rapid Commun. Mass Spectrom. 8:1994;89.
27. Di Donna L., Napoli A., Siciliano C., Sindona G. Int. J. Mass Spectrom. 210/211:2001;165-172.
28. Liguori A., Napoli A., Sindona G. J. Mass Spectrom. 35:2000;139.
29. Hunter E.P.L., Lias S.G. J. Phys. Chem. Ref. Data. 27:1988.
30. Dill J.D., Allen L.C., Topp W.C., Pople J.A. J. Am. Chem. Soc. 97:1975;7220.
31. Jorgensen W.L., Gao J. J. Phys. Chem. 90:1986;2174.
32. Gao J., Garner D.S., Jorgensen W.L. J. Am. Chem. Soc. 108:1986;4784.
33. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J.A. Jr, Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Rega N., Salvador P., Dannenberg J.J., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S., Pople J.A. Gaussian 98, Rev. A.11.3. 2002;Gaussian, Inc, Pittsburgh, PA.
34. North A.C.T., Philips D.C., Mathews F.S. Acta Crystallogr. A. 24:1968;351.
35. SHELXTL NT, Version 5.10; Bruker Analytical X-ray Instruments Inc.: Madison, WI, 1998.
36. Nardelli M. Comput. Chem. 7:1983;95.
37. Schimanski A., Freisinger E., Erxleben A., Lippert B. Inorg. Chim. Acta. 283:1998;223. and references cited therein.
38. De Nino A., Mazzotti F., Perri E., Procopio A., Raffaelli A., Sindona G. J. Mass Spectrom. 35:2000;461.
39. Di Donna, L.; Napoli, A.; Sindona, G. In Advances in Mass Spectrometry Vol XV; Gelpi, E., Ed.; John Wiley and Sons, Ltd.: Chichester, England 2001; pp 765-766.
40. Armentrout P.B. J. Am. Chem. Soc. Mass Spectrom. 11:2000;371.
41. Marsh R.E., Bierstedt R., Eichhorn E.L. Acta Crystallogr. 15:1962;310.
42. Fujinami F., Ogawa K., Arakawa Y., Shirotake S., Fujii S., Tomita K. Acta Crystallogr. B. 35:1979;968.
43. Chen L., Cai L., Zhang X., Rich A. Biochemistry. 33:1994;13540.
44. Salam M.D., Aoki K. Inorg. Chim. Acta. 311:2000;15.
45. Kistenmacher T.J., Rossi M., Marzilli L.G. Biopolymers. 17:1978;2581.
46. Kistenmacher T.J., Rossi M., Caradonna J.P., Marzilli L.G. Adv. Mol. Relaxation Interact. Processes. 15:1979;119.
47. Kistenmacher T.J., Rossi M., Chiang C.C., Caradonna J.P., Marzilli L.G. Adv. Mol. Relaxation Interact. Processes. 17:1980;113.
48. Shaw B.R., Williams N.G., Williams L.D. J. Am. Chem. Soc. 111:1989;7205.
49. Beijer F.H., Sijbesma R.P., Vekemans J.A.J.M., Meijer E.W., Kooijman H., Speck A.L. J. Org. Chem. 61:1996;6371.
50. Izatt R.M., Christensen J.J., Rytting J.H. Chem. Rev. 71:1971;439.