Photoreaction at 5′-(G/C)AABrUT-3′ sequence in duplex DNA: Efficent generation of uracil-5-yl radical by charge transfer

Journal of the American Chemical Society

Volumn 129, Issue 26, 2007, Pages 8163-8168

  Watanabe, Takayoshi ^a   Tashiro, Ryu ^b   Sugiyama, Hiroshi ^b  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; DERIVATIVES; OLIGONUCLEOTIDES; PHOTOCHEMICAL REACTIONS; PROTEINS; SUBSTITUTION REACTIONS;

CYTOSINE DERIVATIVES; PHOTOIRRADIATION; PURINES;

DNA SEQUENCES;

ADENINE; CYTOSINE DERIVATIVE; DOUBLE STRANDED DNA; LACTONE DERIVATIVE; OLIGONUCLEOTIDE; PURINE DERIVATIVE; RADICAL; URACIL; DNA; DRUG DERIVATIVE; GUANINE;

3' UNTRANSLATED REGION; 5' UNTRANSLATED REGION; ANALYTIC METHOD; ARTICLE; BASE PAIRING; ELECTRON TRANSPORT; GENE SEQUENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZATION; PHOTOCHEMISTRY; PROTEIN DNA INTERACTION; REACTION ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; NUCLEOTIDE SEQUENCE;

ADENINE; BASE SEQUENCE; DNA; GUANINE; LIGHT; MODELS, MOLECULAR; PHOTOCHEMISTRY; PURINES; URACIL;

EID: 34447135627     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0692736     Document Type: Article

References (37)

1. (a) Howard-Flanders, F.; Boyce, R. P.; Thenot, L. Nature 1962, 195, 51.
2. (b) Rupp, W. D.; Prusoff, W. H. Nature 1964, 202, 1288.
3. (a) Blatter, E. H.; Ebright, Y. W.; Ebright, R. H. Nature 1992, 359, 650.
4. (b) Willis, M. C.; Hicke, B. J.; Uhlenbeck, O. C.; Cech, T. R.; Koch, T. H. Science 1993, 262, 1255.
5. (c) Hicke, B. J.; Willis, M. C.; Koch, T. H.; Cech, T. R. Biochemistry 1994, 33, 3364.
6. (d) Ogata, R.; Gilbert, W. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 4973.
7. (a) Xu, Y.; Sugiyama, H. Angew. Chem., Int. Ed. 2006, 45, 1354.
8. (b) Sugiyama, H.; Tsutsumi, Y.; Saito, I. J. Am. Chem. Soc. 1990, 112, 6720.
9. (c) Sugiyama, H.; Tsutsumi, Y.; Fujimoto, K.; Saito, I. J. Am. Chem. Soc. 1993, 115, 4443.
10. (d) Sugiyama, H.; Fujimoto, K.; Saito, I.; Kawashima, E.; Sekine, T.; Ishido, Y. Tetrahedron Lett. 1996, 37, 1805.
11. (e) Sugiyama, H.; Fujimoto, K.; Saito, I. Tetrahedron Lett. 1997, 38, 8057.
12. (f) Kawai, K.; Saito, I.; Sugiyama, H. J. Am. Chem. Soc. 1999, 121, 1391.
13. (g) Kawai, K.; Saito, I.; Kawashima, E.; Ishido, R.; Sugiyama, H. Tetrahedron Lett. 1999, 40, 2589.
14. (h) Oyoshi, T.; Kawai, K.; Sugiyama, H. J. Am. Chem. Soc. 2003, 125, 1526.
15. (i) Xu, Y.; Sugiyama, H. J. Am. Chem. Soc. 2004, 126, 6274.
16. (j) Tashiro, R.; Sugiyama, H. J. Am. Chem. Soc. 2003, 125, 15282.
17. (k) Oyoshi, T.; Wang, A. H.-J.; Sugiyama, H. J. Am. Chem. Soc. 2002, 124, 2086.
18. Fujimoto, K.; Sugiyama, H.; Saito, I. Tetrahedron Lett. 1998, 39, 2137-2140.
19. (m) Xu, Y.; Tashiro, R.; Sugiyama, H. Nat. Protoc. 2007, 2, 78-87.
20. (a) Ito, T.; Rokita, S. E. J. Am. Chem. Soc. 2003, 125, 11480.
21. (b) Ito, T.; Rokita, S. E. Angew. Chem., Int. Ed. 2004, 43, 1839.
22. Tashiro, R.; Wang, A. H.-J.; Sugiyama, H. Proc. Natl Acad. Sci. U.S.A. 2006, 103, 16655.
23. Watanabe, T.; Bando, T.; Xu, Y.; Tashiro, R.; Sugiyama, H. J. Am. Chem. Soc. 2005, 127, 44.
24. (a) Cook, G, P.; Greenberg, M, M. J. Am. Chem. Soc. 1996, 118, 10025.
25. (b) Chen, T.; Cook, G. P.; Koppisch, A. T.; Greenberg, M. M. J. Am. Chem. Soc. 2000, 122, 3861.
26. (a) Lewis, F. D.; Letsinger, R. L.; Wasielewski, M. R. Acc. Chem. Res. 2001, 34, 159.
27. (b) Lewis, F. D.; Wu, Y. J. Photochem. Photobiol: C 2001, 2, 1.
28. Ikeda, H.; Saito, I. J. Am. Chem. Soc. 1999, 121, 10836.
29. (a) Kawai, K.; Wata, Y.; Hara, M.; Tojo, S.; Majima, T. J. Am. Chem. Soc. 2002, 124, 3586.
30. (b) Kawai, K.; Osakada, Y.; Fujitsuka, M.; Majima, T. Chem. Biol. 2005, 12, 1049.
31. Kelley, S. O.; Barton, J. K. Science 1999, 283, 15.
32. Valis, L.; Wang, Q.; Raytchev, M.; Buchvarov, I.; Wagenknecht, H. A.; Fiebig, T. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 10192.
33. Lewis, F. D.; Liu, J.; Weigel, W.; Rettig, W.; Kurnikov, I. V.; Beratan, D. N. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 12536.
34. Senthilkumar, K.; Grozema, F. C.; Guerra, C. F.; Bickelhaupt, F. M.; Lewis, F. D.; Berlin, Y. A.; Ratner, M. A.; Siebbeles, L. D. A. J. Am. Chem. Soc. 2005, 127, 14894.
35. Rivera, E.; Schuler, R. H. J. Phys. Chem. 1983, 87, 3966.
36. Wagenknect, H.-A. Charge Transfer in DNA; Wiley-VCH: Weinheim, Germany, 2005; pp 77-91.
37. Stemp, E. D. A.; Arkin, M. R.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 2921.