Rapid radical formation by DNA charge transport through sequences lacking intervening guanines

Journal of the American Chemical Society

Volumn 125, Issue 22, 2003, Pages 6640-6641

  Yoo, Jae ^a   Delaney, Sarah ^a   Stemp, Eric D A ^a   Barton, Jacqueline K ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA; GUANINE DERIVATIVE;

ARTICLE; BASE PAIRING; BINDING SITE; CATION TRANSPORT; COMPUTER ASSISTED TOMOGRAPHY; DNA CHARGE TRANSPORT; DNA DETERMINATION; DNA SEQUENCE; ELECTRON TRANSPORT; OXIDATIVE STRESS; SPECTROSCOPY; TIME;

BASE SEQUENCE; CATIONS; DNA; ELECTROSTATICS; FREE RADICALS; GUANINE; INDOLES; INTERCALATING AGENTS; LUMINESCENT MEASUREMENTS; NUCLEOSIDES; ORGANOMETALLIC COMPOUNDS; OXIDANTS; PHENAZINES; RUTHENIUM; SPECTRUM ANALYSIS;

EID: 0037871659     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034326u     Document Type: Article

References (28)

1. (a) Nunez, M. E.; Barton, J. K.; Curr. Opin. Chem. Biol. 2000, 4, 199.
2. (b) Boon, E. M.; Barton, J. K. Curr. Opin. Struct. Biol. 2002, 12, 320.
3. (a) Lewis, F. D.; Letsinger, R. L.; Wasielewski, M. R. Acc. Chem. Res. 2001, 34, 159.
4. (b) Schuster, G. B. Acc. Chem. Res. 2000, 33, 253.
5. (c) Giese, B. Acc. Chem. Res. 2000, 33, 631.
6. (a) Nunez, M. E.; Hall, D. B.; Barton, J. K. Chem. Biol. 1999, 6, 85.
7. (b) Hall, D. B.; Holmlin, R. E.; Barton, J. K. Nature 1996, 382, 731-735.
8. Ly, D.; Sanii, L.; Schuster, G. B. J. Am. Chem. Soc. 1999, 121, 9400.
9. (a) Giese, B.; Amaudrut, J.; Köhler, A.-K.; Spormann, M.; Wessely, S. Nature 2001, 412. 318-320.
10. (b) Kendrick, T.; Giese, B. Chem. Commun. 2002, 18, 2016.
11. (a) Bixon, M.; Jortner, J. J. Am. Chem. Soc. 2001, 123, 12556.
12. (b) Grozema, F. C.; Berlin, Y. A.; Siebbeles, L. D. A. J. Am. Chem. Soc. 2000, 122, 10903.
13. Henderson, P. T.; Jones, D.; Hampikian, G.; Kan, Y.; Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 8353.
14. (a) Wan, C.; Fiebig, T.; Kelley, S. O.; Treadway, C. R.; Barton, J. K.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 6014.
15. (b) Wan, C.; Fiebig, T.; Schiemann, O.; Barton, J. K.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 14052.
16. (a) Arkin, M. R.; Stemp, E. D. A.; Coates Pulver, S. Chem. Biol. 1997, 4, 389.
17. (b) Wagenknecht, H. A.; Stemp, E. D. A.; Barton, J. K. J. Am. Chem. Soc. 2000, 122, 1.
18. Stemp, E. D. A.; Arkin, M. R.; Barton, J. K. J. Am. Chem. Soc. 1997, 119, 2921.
19. 2+, guanine, and methylindole.
20. Pascaly, M.; Yoo, J.; Barton, J. K. J. Am. Chem. Soc. 2002, 124, 9083.
21. Similar results are seen with a mixed AT sequence intervening.
22. Bhattacharya, P. K.; Barton, J. K. J. Am. Chem. Soc. 2001. 123, 8649.
23. Boon, E. M.; Ceres, D. M.; Drummond, T. G.; Hill, M. G.; Barton, J. K. Nat. Biotechnol. 2000, 18, 1096.
24. This contrasts an earlier suggestion that mismatches affect radical trapping, see: Giese, B.; Wessely, S. Angew. Chem., Int. Ed. 2000, 39, 3490. Also, no A or I radical intermediates are detected.
25. The oxidation potential for I is ≅ 1.5 V. see: Hush, N. S.; Cheung, A. S. Chem. Phys. Lett. 1975, 34, 11.
26. We examined oxidative damage in these assemblies owing to the well characterized reactivity of the GGG site.
27. 2, is observed under these conditions.
28. A sensitivity in long-range oxidative damage to the sequence near hole injection was seen also with capped anthraquinone photooxidants, see Sanii, L.; Schuster, G. B. J. Am. Chem. Soc. 2000, 122, 11545.