Isolation and characterization of a novel product, 2′-deoxyoxanosine, from 2′-deoxyguanosine, oligodeoxynucleotide, and calf thymus DNA treated by nitrous acid and nitric oxide

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2515-2516

  Suzuki, Toshinori ^a   Yamaoka, Ryohei ^a   Nishi, Masatoshi ^b   Ide, Hiroshi ^a   Makino, Keisuke ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

^b SETSUNAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXYOXANOSINE; GUANOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029989276     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja952550g     Document Type: Article

References (21)

1. (a) Gierer, A.; Mundry, K. W. Nature 1958, 182, 1457-1458.
2. (b) Schuster, V. H.; Schramm, G. Z. Naturforsch. 1958, 136, 697-704.
3. (c) Geiduschek, E. P. Proc. Natl. Acad. Sci. U.S.A. 1961, 47, 950-955.
4. (d) Horn, E. E.; Herriott, R. M. Proc. Natl. Acad. Sci. U.S.A. 1962, 48, 1409-1416.
5. Schuster, V. H. Z. Naturforsch. 1960, 156, 298-304.
6. Schuster, V. H.; Wilhelm, R. C. Biochim. Biophys. Acta 1963, 68, 554-560.
7. (a) Shapiro, R. J. Am. Chem. Soc. 1964, 86, 2948-2949.
8. (b) Shapiro, R.; Pohl, S. H. Biochemistry 1968, 7, 448-455.
9. (a) Shapiro, R.; Dubelman, S.; Feinberg, A. M.; Crain, P. F.; McCloskey, J. A. J. Am. Chem. Soc. 1977, 99, 302-303.
10. (b) Dubelman, S.; Shapiro, R. Nucleic Acids Res. 1977, 4, 1815-1827.
11. (a) Kirchner, J. J.; Hopkins, P. B. J. Am. Chem. Soc. 1991, 113, 4681-4682.
12. (b) Kirchner, J. J.; Sigurdsson, S. T.; Hopkins, P. B. J. Am. Chem. Soc. 1992, 114, 4021-4027.
13. Moschel, R. C.; Keefer, L. K. Tetrahedron Lett. 1989, 30, 1467-1468.
14. 5: C, 44.78; H, 4.51; N, 20.89. Found: C, 44.75; H, 4.49; N, 20.90.
15. 2O as an external standard (30.0 ppm).
16. Kato, K.; Yagisawa, N.; Shimada, N.; Hamada, M.; Takita, T.; Maeda, K.; Umezawa, H. J. Antibiot. 1984, 37, 941-942.
17. (a) Shimada, N.; Yagisawa, N.; Naganawa, H.; Takita, T.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1981, 34, 1216-1218.
18. (b) Nakamura, H.; Yagisawa, N.; Shimada, N.; Takita, T.; Umezawa, H.; Iitaka, Y. J. Antibiot. 1981, 34, 1219-1221.
19. Itoh, O.: Kuroiwa, S.; Atsumi, S.; Umezawa, K.; Takeuchi, T.; Hori, M. Cancer Res. 1989, 49, 996-1000.
20. (a) 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, 1001-1003.
21. (b) Nguyen, T.; Brunson, D.; Crespi, C. L.; Penman, B. W.; Wishnok, J. S.; Tannenbaum, S. R. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3030-3034.