Hole trapping at N6-cyclopropyldeoxyadenosine suggests a direct contribution of adenine bases to hole transport through DNA

Journal of the American Chemical Society

Volumn 125, Issue 34, 2003, Pages 10154-10155

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

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADENINE; DNA BASE; N6 CYCLOPROPYLDEOXYADENOSINE; UNCLASSIFIED DRUG;

ARTICLE; DNA SYNTHESIS; DNA TRANSFER; ELECTRON TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION REDUCTION REACTION; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPIN TRAPPING;

EID: 0042933789     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035887o     Document Type: Article

References (33)

1. Núñez, M. E.; Hall, D. B.; Barton, J. K. Chem. Biol. 1999, 6, 85-97.
2. Giese, B. Annu. Rev. Biochem. 2002, 71, 51-70.
3. Lewis F. D.; Wu, T.; Letsinger, R. L.; Wasielewski, M. R. Acc. Chem. Res. 2001, 34, 159-170.
4. Schuster, G. B. Acc. Chem. Res. 2000, 33, 253-260.
5. (a) Nakatani, K.; Dohno, C.; Saito, I. J. Am. Chem. Soc. 1999, 121, 10854-10855.
6. (b) Nakatani, K.; Dohno, C.; Saito, I. J. Am. Chem. Soc. 2000, 122, 5893-5894.
7. (c) Nakatani, K.; Dohno, C.; Saito, I. J. Am. Chem. Soc. 2002, 124, 6802-6803.
8. (d) Nakatani, K.; Dohno, C.; Ogawa, A.; Saito I. Chem. Biol. 2002, 9, 361-366.
9. (e) Dohno, C.; Nakatani, K.; Saito I. J. Am. Chem. Soc. 2002, 124, 14580-14585.
10. (a) Jortner, J.; Bixon, M.; Langenbacher, T.; Michel-Beyerle, M. E. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 12759-12765.
11. (b) Grozema, F. C.; Berlin, Y. A.; Siebbeles, L. D. A. J. Am. Chem. Soc. 2000, 122, 10903-10909.
12. (c) Berlin, Y. A.; Burin, A. L.; Ratner, M. A. Chem. Phys. 2002, 275, 61-74.
13. (a) Seidel, C. A.; Schulz, A.; Sauer, M. H. M. J. Phys. Chem. 1996, 100, 5541-5553.
14. (b) Steenken, S.; Jovanovic, S. V. J. Am. Chem. Soc. 1997, 119, 617-618.
15. (a) Williams, T. T.; Odom, D. T.; Barton, J. K. J. Am. Chem. Soc. 2000, 122, 9048-9049.
16. (a) Henderson, P. T.; Jones, D.; Hampikian, G.; Kan, Y.; Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 8353-8358.
17. (b) Sartor, V.; Boone, Edna.; Schuster, G. B. J. Phys. Chem. B 2001, 105, 11057-11059.
18. (c) Barnett, R. N.; Cleveland, C. L.; Joy, A.; Landman, U.; Schuster, G. B. Science 2001, 294, 567-571.
19. (a) Giese, B.; Spichty, M. ChemPhysChem 2000, 1, 195-198.
20. (b) Giese, B.; Amaudrut, J.; Köhler, A.-K.; Spormann, M.; Wessely, S. Nature 2001, 412, 318-320.
21. (c) Kendrick, T.; Giese, B. Chem. Commun. 2002, 2016-2017.
22. (a) Bixon, M.; Jortner, J. J. Am. Chem. Soc. 2001, 123, 12556-12567.
23. (b) Bixon, M.; Jortner, J. Chem. Phys. 2002, 281, 393-408.
24. Nakatani, K.; Dohno, C.; Saito, I. J. Am. Chem. Soc. 2001, 123, 9681-9682.
25. (a) Musa, O. M.; Horner, J. H.; Shahin, H.; Newcomb, M. J. Am. Chem. Soc. 1996, 118, 3862-3868.
26. (b) Bouchoux, G.; Alcaraz, C.; Dutuit, O.; Nguyen, M. T. J. Am. Chem. Soc. 1998, 120, 152-160.
27. (c) Loeppky, R. N.; Elomari, S. J. Org. Chem. 2000, 65, 96-103.
28. (d) Shaffer, C. L.; Morton, M. D.; Hanzlik, R. P. J. Am. Chem. Soc. 2001, 123, 8502-8508.
29. (a) Ceulemans, G.; Busson, R.; Weyns, N.; Vandendriessche, F.; Rozenski, J.; Izerman, A.; Herdewijn, P. Nucleosides Nucleotides 1994, 13, 1991-2000.
30. (b) Kim, H. Y.; Nechev, L.; Zhou, L.; Tamura, P.; Harris, C. M.; Harris, T. Tetrahedron Lett. 1998, 41, 6803-6806.
31. (c) Veliz, E. A.; Beal, P. A. Tetrahedron Lett. 2000, 41, 1695-1697.
32. CPA radical species from the methyl group of thymine. Tandem reactions may contribute to the cleavage bands in Figure 2.
33. HPA is detected.