Chemical synthesis of cross-link lesions found in nitrous acid treated DNA: A general method for the preparation of N2-substituted 2'- deoxyguanosines

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 2959-2964

  Harwood, Eric A ^a   Hopkins, Paul B ^a   Sigurdsson, Snorri Th ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DEOXYGUANOSINE DERIVATIVE; NITROUS ACID;

ARTICLE; DNA CROSS LINKING; DNA STRUCTURE; REACTION ANALYSIS;

CATALYSIS; CROSS-LINKING REAGENTS; DEOXYGUANOSINE; DNA; INDICATORS AND REAGENTS; NITROUS ACID; PALLADIUM; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0034686069     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991501+     Document Type: Article

References (35)

1. Zimmerman, F. K. Mutat. Res. 1977, 39, 127-147.
2. Environmental Health Criteria 5, Nitrates, Nitrites, and N - Nitroso Compounds; World Health Organization: Geneva, 1978.
3. Handbook of Food Additives; 2nd ed.; Furia, T. E., Ed.; CRC press: Cleveland, 1972; pp 150-155.
4. Wakabayashi, K. Mutation and the Environment, Part E: Environmental Genotoxicity, Risk, and Modulation; Wiley-Liss: New York, 1990; pp 107-116.
5. Shapiro, R.; Dubelman, S.; Feinberg, A. M.; Crain, P. F.; McCloskey, J. A. J. Am. Chem. Soc. 1977, 99, 302-303.
6. Kirchner, J. J.; Solomon, M. S.; Hopkins, P. B. In Structure and Function: Proceedings of the Seventh Conversation in Biomolecular Stereodynamics; Sarma, R. H., Sarma, M. H., Eds.; Adenine Press: Albany, 1992; pp 171-182.
7. Harwood: E. A.; Sigurdsson, S. T.; Edfeldt, N. B. F.; Reid, B. R.; Hopkins, P. B. J. Am. Chem. Soc. 1999, 121, 5081-5082.
8. Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090-6091.
9. Lee, H.; Hinz, M.; Stezowski, J. J.; Harvey, R. G. Tetrahedron Lett. 1990, 31, 6773-6776.
10. Schmid, N.; Behr, J. P. Tetrahedron Lett. 1995, 36, 1447-1450.
11. Tsarouhtsis, D.; Kuchimanchi, S.; DeCorte, B. L.; Harris, C. M.; Harris, T. M. J. Am. Chem. Soc. 1995, 117, 11013-11014.
12. DeCorte, B. L.; Tsarouhtsis, D.; Kuchimanchi, S.; Cooper, M. D.; Horton, P.; Harris, C. M.; Harris, T. M. Chem. Res. Toxicol. 1996, 9, 630-637.
13. Bonala, R. R.; Yu, P. L.; Johnson, F. Tetrahedron Lett. 1999, 40, 597-598.
14. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
15. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7241.
16. Woo, J.; Sigurdsson, S. T.; Hopkins, P. B. J. Am. Chem. Soc. 1993, 115, 3407-3415.
17. Acedo, M.; Fabrega, C.; Avino, A.; Goodman, M.; Fagan, P.; Wemmer, D.; Eritja, R. Nucleic Acids Res. 1994, 22, 2982-2989.
18. Kirchner, J. J.; Sigurdsson, S. T.; Hopkins, P. B. J. Am. Chem. Soc. 1992, 114, 4021-4027.
19. Lawley, P. D. Br. Med. Bull. 1980, 36, 19-24.
20. Lawley, P. D. BioEssays 1995, 17, 561-568.
21. Harvey, R. G.; Geacintov, N. E. Acc. Chem. Res. 1988, 21, 66.
22. Polycyclic Hydrocarbons and Carcinogenesis; Harvey, R. G., Ed.; American Chemical Society: Washington, D. C., 1985; pp 1 ff.
23. Tomasz, M.; Chowdary, D.; Lipman, R.; Shimotakahara, S.; Veiro, D.; Walker, V.; Verdine, G. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 6702.
24. Lewis, M. A.; Yoerg, D. G.; Bolton, J. L.; Thompson, J. A. Chem. Res. Toxicol. 1996, 9, 1368-1374.
25. Edwards, C.; Boche, G.; Steinbrecher, T.; Scheer, S. J. Chem. Soc., Perkin Trans. 1 1997, 1887-1893.
26. Focher, F.; Hildebrand, C.; Freese, S.; Ciarrochi, G.; Noonan, T.; Sangalli, S.; Brown, N.; Spadari, S.; Wright, G. J. Med. Chem. 1988, 31, 1496-1500.
27. Focher, F.; Hildebrand, C.; Sangalli, S.; Sandoli, D.; Ciarrocchi, G.; Rebuzzini, A.; Pedrali-Noy, G.; Manservigi, R.; Wright, G.; Brown, N.; Spadari, S. Methods Findings Exptl. Clin. Pharmocol. 1989, 11, 577-582.
28. Hildebrand, C.; Sandoli, D.; Focher, F.; Gambino, J.; Ciarrocchi, G.; Spadari, S.; Wright, G. J. Med. Chem. 1990, 33, 203-206.
29. Khan, N. N.; Wright, G. E.; Dudycz, L. W.; Brown, N. C. Nucleic Acids Res. 1984, 12, 3695.
30. Wright, G. E.; Dudycz, L. W. J. Med. Chem. 1984, 27, 175-181.
31. Wright, G. E.; Dudycz, L. W.; Kazimierczuk, Z.; Brown, N. C.; Khan, N. N. J. Med. Chem. 1987, 30, 109-116.
32. Xu, H.; Maga, G.; Focher, F.; Smith, E. R.; Spadari, S.; Gambino, J.; Wright, G. E. J. Med. Chem. 1995, 38, 49-57.
33. Potter, G. A.; McCague, R.; Jarman, M. J. Chem. Soc., Chem. Commun. 1992, 637-638.
34. De Riccardis, F.; Bonala, R.; Johnson, F. J. Am. Chem. Soc. 1999, 121, 10453-10460.
35. De Riccardis, F.; Johnson, F. Org. Lett. 2000, 2, 293-295.