Pyrimidine ring opening in the unimolecular dediazoniation of guanine diazonium ion. An ab initio theoretical study of the mechanism of nitrosative guanosine damination

Journal of the American Chemical Society

Volumn 118, Issue 44, 1996, Pages 10942-10943

  Glaser, Rainer ^a   Son, Man Shick ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CALCULATION; DRUG SYNTHESIS; MOLECULAR DYNAMICS; REACTION ANALYSIS; THEORY;

EID: 0029849366     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961334k     Document Type: Article

References (22)

1. DNA Damage and Cytotoxicity Caused by Nitric Oxide. Tannenbaum, S. R.; Tamir, S.; Rojas-Walker, T. d.; Wishnok, J. S. In Nitrosamines and Related N-Nitroso Compounds - Chemistry and Biochemistry; Loeppky, R N., Michejda, C. L., Eds.; ACS Symposium Series 553; American Chemical Society: Washington, DC, 1994; Chapter 10, p 120.
2. Wink, D. A.; Kasprzak, K. S.; Maragos, C. M.; Elespuru, R. K.; Misra, M.; Dunams, T. M.; Cebula, T. A.; Koch, W. H.; Andrews, A. W.; Allen, J. S.; Keefer, L. K. Science 1991, 254, 1001 and references therein.
3. Nair, V.; Chamberlain, S. D. Synthesis 1984, 401-403 and references therein.
4. Duncan, B. K.; Miller, J. H. Nature 1980, 287, 560.
5. Chen, H.; Shaw, B. R. Biochemistry 1993, 32, 3535.
6. Becker, E. F., Jr.; Zimmerman, B. K.; Geiduschek, E. P. J. Mol. Biol. 1964, 8, 377.
7. Alberts, B. M.; Doty, P. J. Mol. Biol. 1968, 32, 379.
8. Shapiro, R.; Dubelman, S.; Feinberg, A. M.; Crain, P. F.; McCloskey, J. A. J. Am. Chem. Soc. 1977, 99, 302.
9. (a) Zollinger, H. Diazo Chemistry I-Aromatic and Heteroaromatic Compounds; VCH: Weinheim, 1994.
10. (b) Ibid; 199.
11. Verly, W. G.; LaCroix, M. Biochim. Biophys. Acta 1975, 414, 185.
12. (a) Kirchner, J. J.; Sigurdsson, S. T.; Hopkins, P, B. J. Am. Chem, Soc. 1992, 114, 4021.
13. (b) Elcock, A. H.; Lyne, P. D.; Mulholland, A. J.; Handra, A.; Richards, W. G. J. Am. Chem, Soc. 1995, 117, 4706.
14. Suzuki, T.; Yamaoka, R.; Nishi, M.; Ide, H.; Makino, K. J. Am. Chem. Soc. 1996, 118, 2515.
15. (a) Glaser, R.; Choy, G. S.-C.; Hall, M. K. J. Am. Chem. Soc. 1991, 113, 1109.
16. (b) Glaser, R.; Horan, C. J.; Haney, P. E. J. Phys. Chem, 1993, 97, 1835.
17. (c) Horan, C. J.: Glaser, R. J. Phys. Chem. 1994, 98, 3989.
18. (d) Glaser, R.; Horan, C. J. J. Org. Chem. 1995, 60, 7518.
19. Guimon, C.; Khayar, S.; Gracian, F.; Begrup, M.; Pfister-Guillouzo, G. Chem. Phys. 1989, 138, 157.
20. Nguyen, M. T.; Hegarty, A. F. J. Chem. Soc., Perkin Trans, 2 1983, 1297.
21. Shapiro, R.; Pohl, S. H. Biochemistry 1968, 7, 448.
22. Luk, K.-C.; Moore, D. W.; Keith, D. D. Tetrahedron Lett. 1994, 35, 1007.