Efficient Synthesis of DNA Containing the Guanine Oxidation-Nitration Product 5-Guanidino-4-nitroimidazole: Generation by a Postsynthetic Substitution Reaction

Organic Letters

Volumn 6, Issue 2, 2004, Pages 245-248

  Neeley, William L ^a   Henderson, Paul T ^a,b   Essigmann, John M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXYNUCLEOSIDE; 5 GUANIDINO 4 NITROIMIDAZOLE; DNA; DOUBLE STRANDED DNA; GUANINE; NITROIMIDAZOLE DERIVATIVE; NUCLEOSIDE DERIVATIVE; OLIGODEOXYNUCLEOTIDE; PEROXYNITRITE; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DNA SYNTHESIS; MELTING POINT; NITRATION; OXIDATION; PROTEIN STABILITY; REACTION ANALYSIS; VIRUS GENOME;

DEOXYGUANOSINE; DNA; GUANIDINES; GUANINE; MOLECULAR STRUCTURE; NITROIMIDAZOLES; OXIDATION-REDUCTION;

EID: 0842328409     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036188j     Document Type: Article

References (32)

1. Cadet, J.; Bellon, S.; Berger, M.; Bourdat, A. G.; Douki, T.; Duarte, V. ; Frelon, S.; Gasparutto, D.; Muller, E.; Ravanat, J. L.; Sauvaigo, S. Biol. Chem. 2002, 383, 933-943.
2. Burney, S.; Niles, J. C.; Dedon, P. C.; Tannenbaum, S. R. Chem. Res. Toxicol. 1999, 12, 513-520.
3. Kornyushyna, O.; Berges, A. M.; Muller, J. G.; Burrows, C. J. Biochemistry 2002, 41, 15304-15314.
4. Lee, J. M.; Niles, J. C.; Wishnok, J. S.; Tannenbaum, S. R. Chem. Res. Toxicol. 2002, 15, 7-14.
5. Tretyakova, N. Y.; Niles, J. C.; Burney, S.; Wishnok, J. S.; Tannenbaum, S. R. Chem. Res. Toxicol. 1999, 12, 459-466.
6. Burrows, C. J.; Muller, J. G.; Kornyushyna, O.; Luo, W.; Duarte, V.; Leipold, M. D.; David, S. S. Environ. Health Perspect. 2002, 110, 713-717.
7. Gu, F.; Stillwell, W. G.; Wishnok, J. S.; Shallop, A. J.; Jones, R. A.; Tannenbaum, S. R. Biochemistry 2002, 41, 7508-7518.
8. Joffe, A.; Mock, S.; Yun, B. H.; Kolbanovskiy, A.; Geacintov, N. E.; Shafirovich, V. Chem. Res. Toxicol. 2003, 16, 966-973.
9. Niles, J. C.; Wishnok, J. S.; Tannenbaum, S. R. J. Am. Chem. Soc. 2001, 123, 12147-12151.
10. Henderson, P. T.; Delaney, J. C.; Gu, F.; Tannenbaum, S. R.; Essigmann, J. M. Biochemistry 2002, 41, 914-921.
11. Kino, K.; Sugiyama, H. Chem. Biol. 2001, 8, 369-378.
12. Shafirovich, V.; Mock, S.; Kolbanovskiy, A.; Geacintov, N. E. Chem. Res. Toxicol. 2002, 15, 591-597.
13. Verma, S.; Eckstein, F. Annu. Rev. Biochem. 1998, 67, 99-134.
14. MacMillan, A. M.; Chen, L.; Verdine, G. L. J. Org. Chem. 1992, 57, 2989-2991.
15. Ikeda, H.; Saito, I. J. Am. Chem. Soc. 1999, 121, 10836-10837.
16. Xu, Y. Z.; Zheng, Q.; Swann, P. F. J. Org. Chem. 1992, 57, 3839-3845.
17. Gao, H.; Fathi, R.; Gaffney, B. L.; Goswami, B.; Kung, P. P.; Rhee, Y.; Jin, R.; Jones, R. A. J. Org. Chem. 1992, 57, 6954-6959.
18. Allerson, C. R.; Chen, S. L.; Verdine, G. L. J. Am. Chem. Soc. 1997, 119, 7423-7433.
19. Haginoya, N.; Ono, A.; Nomura, Y.; Ueno, Y.; Matsuda, A. Bioconjugate Chem. 1997, 8, 271-280.
20. Kohgo, S.; Shinozuka, K.; Ozaki, H.; Sawai, H. Tetrahedron Lett. 1998, 39, 4067-4070.
21. MacMillan, A. M.; Verdine, G. L. J. Org. Chem. 1990, 55, 5931-5933.
22. MacMillan, A. M.; Verdine, G. L. Tetrahedron 1991, 47, 2603-2616.
23. Del Carmen, M.; Barrio, G.; Scopes, D. I. C.; Holtwick, J. B.; Leonard, N. J. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 3986-3988.
24. Gallo, G. G.; Pasqualucci, C. R.; Radaelli, P.; Lancini, G. C. J. Org. Chem. 1964, 29, 862-865.
25. Rousseau, R. J.; Robins, R. K.; Townsend, L. B. J. Am. Chem. Soc. 1968, 90, 2661-2668.
26. Carbon, J. A. J. Org. Chem. 1961, 26, 455-461.
27. Hasan, A.; Lambert, C. R.; Srivastava, P. C. J. Heterocycl. Chem. 1990, 27, 1877-1883.
28. Petersson, A. S.; Steen, H.; Kalume, D. E.; Caidahl, K.; Roepstorff, P. J. Mass Spectrom. 2001, 36, 616-625.
29. Sarver, A.; Scheffler, N. K.; Shetlar, M. D.; Gibson, B. W. J. Am. Soc. Mass Spectrom. 2001, 12, 439-448.
30. Plum, G. E.; Grollman, A. P.; Johnson, F.; Breslauer, K. J. Biochemistry 1995, 34, 16148-16160.
31. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
32. Henderson, P. T.; Delaney, J. C.; Muller, J. G.; Neeley, W. L.; Tannenbaum, S. R.; Burrows, C. J.; Essigmann, J. M. Biochemistry 2003, 42, 9257-9262.