p-Cyano substituted 5-benzoyldeoxyuridine as a novel electron-accepting nucleobase for one-electron oxidation of DNA

Tetrahedron Letters

Volumn 39, Issue 33, 1998, Pages 5995-5998

  Nakatani, Kazuhiko ^a   Fujisawa, Kazuhiko ^a   Dohno, Chikara ^a   Nakamura, Takashi ^a   Saito, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 BENZOYLDEOXYURIDINE; DEOXYURIDINE DERIVATIVE; DNA; IMIDAZOLE DERIVATIVE; NUCLEIC ACID BASE; PHOSPHORAMIDIC ACID DERIVATIVE; PIPERIDINE; UNCLASSIFIED DRUG;

ARTICLE; DNA CLEAVAGE; DNA SYNTHESIS; ELECTRON; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRRADIATION; OXIDATION;

EID: 0032514559     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01231-3     Document Type: Article

References (21)

1. (1) For reviews, see: (a) Arkin, M. R.; Stemp, E. D. A.; Pulver, S. C.; Barton, J. K. Chem. Biol. 1997 4, 389-400.
2. (b) Holmlin, R. E.; Dandliker, P. J.; Barton, J. K. Angew. Chem. Int. Ed. Engl. 1997, 36, 2714-2730.
3. (2) (a) Murphy, C. J.; Arkin, M. R.; Jenkins, Y.; Ghatila, N. D.; Bossmann, S. H.; Turro, N. J.; Barton, J. K. Science, 1993, 262, 1025-1029.
4. (b) Hall, D. B.; Holmlin, R. E.; Barton, J. K. Nature 1996, 382, 731-735.
5. (c) Hall, D. B.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 5045-5046.
6. (3) (a) Gasper, S. M.; Schuster, G. B. J. Am. Chem. Soc. 1997, 119, 12762-12771.
7. (b) Armitage, B.; Ly, D.; Koch, T.; Frydenlund, H.; Ørum, H.; Bats, H. G.; Schuster, G. B. Proc. Natl. Acad. Sci. USA 1997, 94, 12320-12325.
8. (4) Lewis, F. D.; Wu, T.; Zhang, Y.; Letsinger, R. L.; Greenfield, S. R.; Wasielewski, M. R. Science, 1997, 277, 673-676.
9. (5) Fukui, K.; Tanaka, K. Angew. Chem. Int. Ed. Engl. 1998, 37, 158-161.
10. (6) Nakatani, K.; Dohno, C.; Nakamura, T, Saito, I. Tetrahedron Lett. 1998, 39, 2779-2782.
11. (7) (a) Armstrong, R. W.; Gupta, S.; Whelihan, F. Tetrahedron Lett. 1989, 30, 2057-2061.
12. (b) Hayakawa, H.; Tanaka, H.; Obi, K.; Itoh, M.; Miyasaka, T. Tetrahedron Lett. 1987, 28, 87-91.
13. + 358.1038, found 358.1054.
14. (9) (a) Saito, I.; Takayama, M.; Kawanishi, S. J. Am. Chem. Soc. 1995, 117, 5590-5591.
15. (b) Saito, I.; Takayama, M.; Sugiyama, H.; Nakatani, K.; Tsuchida, A.; Yamamoto, M. J. Am. Chem. Soc. 1995, 117, 6406-6407.
16. (c) Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063-7068.
17. (d) Saito, I.; Nakatani, K. Bull. Chem. Soc. Jpn. 1996, 69, 3007-3019.
18. (e) Saito, I.; Takayama, M.; Sugiyama, H.; Nakamura, T. J. Photochem. Photobiol. A 1997, 106, 141-144.
19. (10) (a) Cadet, J.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Raoul, S.; Ravanat, J. -L. J. Am. Chem. Soc. 1994, 116, 7403-7404.
20. (b) Raoul, S.; Berger, M.; Buchko, G. W.; Joshi, P. C.; Morin, B.; Weifeld, M.; Cadet, J. J. Chem. Soc., Perkin Trans. 2 1996, 371-381.
21. (c) Cullis, P. M.; Malone, M. E.; Merson-Davis, L. A. J. Am. Chem. Soc. 1996, 118, 2775-2781.