Chemistry of sequence-dependent remote guanine oxidation: Photoreaction of duplex DNA containing cyanobenzophenone-substituted uridine [14]

Journal of the American Chemical Society

Volumn 121, Issue 46, 1999, Pages 10854-10855

  Nakatani, Kazuhiko ^a   Dohno, Chikara ^a   Saito, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE DERIVATIVE; DOUBLE STRANDED DNA; GUANINE; URIDINE DERIVATIVE;

BASE PAIRING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRRADIATION; LETTER; NONHUMAN; NUCLEOTIDE SEQUENCE; OXIDATION; PHOTOREACTIVITY;

EID: 0033601114     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9920213     Document Type: Letter

References (31)

1. For recent reviews, see: (a) Holmlin, R. L.; Dandliker, P. J.; Barton, J. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2714-2730. (b) Beratan, D. N.; Priyadarshy, S.; Risser, S. M. Chem. Biol. 1997, 4, 3-8. (c) Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109-1154.
2. For recent reviews, see: (a) Holmlin, R. L.; Dandliker, P. J.; Barton, J. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2714-2730. (b) Beratan, D. N.; Priyadarshy, S.; Risser, S. M. Chem. Biol. 1997, 4, 3-8. (c) Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109-1154.
3. For recent reviews, see: (a) Holmlin, R. L.; Dandliker, P. J.; Barton, J. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2714-2730. (b) Beratan, D. N.; Priyadarshy, S.; Risser, S. M. Chem. Biol. 1997, 4, 3-8. (c) Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109-1154.
4. (a) Núñez, M. E.; Hall, D. B.; Barton, J. K. Chem. Biol. 1999, 6, 85-97.
5. (b) Hall, D. B.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 5045-5046.
6. (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.; Orum, H.; Batz, H. G.; Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 12320-12325.
8. Lewis, F. D.; Wu, T.; Zhang, Y.; Letsinger, R. L.; Greenfield, S. R.; Wasielewski, M. R. Science 1997, 277, 673-676.
9. Fukui, K.; Tanaka, K. Angew. Chem., Int. Ed. 1998, 37, 158-161.
10. (a) Hall, D. B.; Kelley, S. O.; Barton, J. K. Biochemistry 1998, 37, 15933-15940.
11. (b) Kelley, S. O.; Barton, J. K. Chem. Biol. 1998, 5, 413-425.
12. (a) Giese, B.; Wessely, S.; Spormann, M.; Lindemann, U.; Meggers, E.; Michel-Beyerle, M. E. Angew. Chem., Int. Ed. 1999, 38, 996-998.
13. (b) Meggers, E.; Michel-Beyerle, M. E.; Giese, B. J. Am. Chem. Soc. 1998, 120, 12950-12955.
14. Kelley, S. O.; Barton, J. K. Science 1999, 283, 375-381.
15. Nakatani, K.; Dohno, C.; Saito, I. J. Org. Chem. 1999, 64, 6901-6904.
16. (a) Nakatani, K.; Dohno, C.; Nakamura, T.; Saito, I. Tetrahedron Lett. 1998, 39, 2779-2782.
17. (b) Nakatani, K.; Fujisawa, K.; Dohno, C.; Nakamura, C.; Saito, I. Tetrahedron Lett. 1998, 39, 5995-5998.
18. (a) Saito, I.; Nakamura, T.; Nakatani, K.; Yoshioka, Y.; Yamaguchi, K.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 12686-12687.
19. (b) Kino, K.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 7373-7374.
20. (c) Saito, I.; Takayama, M.; Sugiyama, H.; Nakatani, K.; Tsuchida, A.; Yamamoto, M. J. Am. Chem. Soc. 1995, 117, 6406-6407.
21. (d) Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063-7068.
22. See Supporting Information for experimental data.
23. d were 4.3% for ODN 9 and 8.7% for ODN 11.
24. •+, leading to piperidine-sensitive product dIz.
25. Jortner, J.; Bixon, M.; Langenbacher, T.; Michel-Beyerle, M. E. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12759-12765.
26. Harriman, A. Angew. Chem., Int. Ed. 1999, 38, 945-949.
27. Heating the photoirradiated duplex with piperidine produced d(GAT-AGT) and d(GAC), confirming the selective oxidation of 5 G of the GG step.
28. CNBPU.
29. (a) 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.
30. (b) Vialas, C.; Pratviel, G.; Claparols, C.; Meunier, B. J. Am. Chem. Soc. 1998, 120, 11548-11553.
31. 11b,19a (21) Under the conditions of the photoreaction and the HPLC analysis, formation of another G oxidation product, 8-oxodG, was not observed.