Synthesis of DNA oligomers containing modified uracil possessing electron-accepting benzophenone chromophore

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6901-6904

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

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPHENONE; DNA; OLIGOMER; URACIL;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; ELECTRON TRANSPORT; NOTE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032886747     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904516     Document Type: Note

References (25)

1. For recent reviews, see: (a) Beratan, D. N.; Priyadarshy, S.; Risser, S. M. Chem. Biol. 1997, 4, 3-8.
2. (b) Holmlin, R. L.; Dandliker, P. J.; Barton, J. K. Angew. Chem., Int. Ed. Engl. 1997, 36, 2714-2730.
3. (c) Burrows, C. J.; Muller, J. G. Chem. Rev. 1998, 98, 1109-1154.
4. For contributions from these laboratories, see: (a) Saito, I.; Takayama, M.; Sugiyama, H.; Nakatani, K.; Tsuchida, A.; Yamamoto, M. J. Am. Chem. Soc. 1995, 117, 6406-6407.
5. (b) Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063-7068.
6. (c) Saito, I.; Takayama, M.; Sugiyama, H.; Nakamura, T. In DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases; Meunier, B., Ed.; NATO ASI Series; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1996; pp 163-176.
7. (d) Saito, I.; Nakatani, K. Bull. Chem. Soc. Jpn. 1996, 69, 3007-3019.
8. (e) Saito, I.; Takayama, M.; Sugiyama, H.; Nakamura, T. J. Photochem. Photobiol. A 1997, 106, 141-144.
9. (f) Kino, K.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 7373-7374.
10. (g) Saito, I.; Nakamura, T.; Nakatani, K.; Yoshioka, Y.; Yamaguchi, K.; Sugiyama, H. J. Am. Chem. Soc. 1998, 120, 12686-12687. See also ref 10.
11. (a) Hall, D. B.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 5045-5046.
12. (b) Hall, D. B.; Holmlin, R. E.; Barton, J. K. Nature 1996, 382, 731-734.
13. (a) Gasper, S. M.; Schuster, G. B. J. Am. Chem. Soc. 1997, 119, 12762-12771.
14. (b) For ET studies using PNA oligomers containing an internally linked anthraquinone chromophore, see: Armitage, B.; Ly, D.; Koch, T.; Frydenlund, H.; Orum, H.; Batz, H. G.; Schuster, G. B. Proc. Natl. Acad. Sci. USA 1997, 94, 12320-12325.
15. Fukui, K.; Tanaka, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 158-161.
16. (a) Kelley, S. O.; Barton, J. K. Chem. Biol. 1998, 5, 413-425.
17. (b) Kelley, S. O.; Holmlin, R. E.; Stemp, E. D. A.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 9861-9870.
18. Lewis, F. D.; Wu, T.; Zhang, Y.; Letsinger, R. L.; Greenfield, S. R.; Wasielewski, M. R. Science 1997, 277, 673-676.
19. (a) Meggers, E.; Michel-Beyerle, M. E.; Giese, B. J. Am. Chem. Soc. 1998, 120, 12950-12955.
20. (b) Meggers, E.; Kusch, D.; Spichty, M.; Wille, U.; Giese, B. Angew. Chem., Int. Ed. Engl. 1998, 37, 460-462.
21. Kelley, S. O.; Barton, J. K. Science 1999, 283, 375-381.
22. (a) Nakatani, K.; Dohno, C.; Nakamura, T.; Saito, I. Tetrahedron Lett. 1998, 39, 2779-2782.
23. (b) Nakatani, K.; Fujisawa, K.; Dohno, C.; Nakamura, C.; Saito, I. Tetrahedron Lett. 1998, 39, 5995-5998.
24. Procházka, M.; Siroky, M. Collect. Czech. Chem. Commun. 1983, 43, 1765-1773.
25. A similar decrease in melting temperature has been reported for oligomers containing bulky phenanthroline-substituted deoxyuridine. See: Hurley, D. J.; Tor, Y. J. Am. Chem. Soc. 1998, 120, 2194-2195.