On the mechanism of long-range electron transfer through DNA

Angewandte Chemie - International Edition

Volumn 38, Issue 7, 1999, Pages 996-998

  Giese, Bernd ^a   Wessely, Stephan ^a   Spormann, Martin ^a   Lindemann, Ute ^a   Meggers, Eric ^a   Michel Beyerle, Maria E ^b  

^a UNIVERSITY OF BASEL   (Switzerland)

^b TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Bioorganic chemistry; DNA oxidation; Electron transfer; Radicals

Indexed keywords

DNA;

ARTICLE; BASE PAIRING; DNA SEQUENCE; DNA STRAND; ELECTRON TRANSPORT; NUCLEOTIDE SEQUENCE; OXIDATION; OXIDATION REDUCTION POTENTIAL;

EID: 0033119286     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990401)38:7<996::AID-ANIE996>3.0.CO;2-4     Document Type: Article

References (30)

1. Comments on charge transfer in DNA: a) D. N. Beratan, S. Priyadarshy, S. M. Risser, Chem. Biol. 1997, 4, 3;
2. b) E. K. Wilson, Chem. Eng. News 1997, 75(8), 33;
3. c) T. L. Netzel J. Chem. Educ. 1997, 74, 646;
4. d) G. Taubes, Science 1997, 275, 1420;
5. e) S. Priyadarshy, S. M. Risser, D. N. Beratan, J. Biol. Inorg. Chem. 1998, 3, 196;
6. f) N. J. Turro, J. K. Barton, J. Biol. Inorg. Chem. 1998, 3, 201;
7. g) T. L. Netzel, J. Biol. Inorg. Chem. 1998, 3, 210;
8. h) F. D. Lewis, R. L. Letsinger, J. Biol. Inorg. Chem. 1998, 3, 215;
9. i) E. S. Krider, T. J. Meade, J. Biol. Inorg. Chem. 1998, 3, 222.
10. a) A. M. Brun, A. Harriman, J. Am. Chem. Soc. 1992, 114, 3656;
11. b) A. M. Brun, A. Harriman, J. Am. Chem. Soc. 1994, 116, 10383;
12. c) S.J. Atherton, P.C. Beaumont, J. Phys. Chem. 1995, 99, 12025;
13. d) F. D. Lewis, T. Wu, Y. Zhang, R. L. Letsinger, S. R. Greenfield, M. R. Wasielewski, Science 1997, 277, 673;
14. e) K. Fukui, K. Tanaka, Angew. Chem. 1998, 110, 167;
15. Angew. Chem. Int. Ed. 1998, 37, 158;
16. f) E. Meggers, D. Kusch, M. Spichty, U. Wille, B. Giese, Angew. Chem. 1998, 110, 474;
17. Angew. Chem. Int. Ed. 1998, 37, 460.
18. a) C. J. Murphy, M. R. Arkin, Y. Jenkins, N. D. Ghatlia, S. H. Bossmann, N. J. Turro, J. K. Barton, Science 1993, 262, 1025;
19. b) S. O. Kelley, R. E. Holmlin, E. D. A. Stemp, J. K. Barton, J. Am. Chem. Soc. 1997, 119, 9861.
20. a) E. Meggers, M. E. Michel-Beyerle, B. Giese, J. Am. Chem. Soc. 1998, 120, 12950;
21. b) J. Jortner, M. Brixon, T. Langenbacher, M. E. Michel-Beyerle, Proc. Natl. Acad. Sci. USA 1998, 95, 12759;
22. see also: c) T. Melvin, S. Botchway, A. W. Parker, P. O. Neill, J. Chem. Soc. Chem. Commun. 1995, 653;
23. d) S. M. Gasper, G. B. Schuster, J. Am. Chem. Soc. 1997, 119, 12762.
24. S. Steenken, S. V. Jovanovic, J. Am. Chem. Soc. 1997, 119, 617.
25. C. A. M. Seidel, A. Schulz, M. H. M. Sauer, J. Phys. Chem. 1996, 100, 5541.
26. S. Steenken, J. P. Telo, H. M. Novais, L. P. Candeias, J. Am. Chem. Soc. 1992, 114, 4701.
27. [4a] the experiments were carried out with 4′-pivaloyl-substituted guanosine. The synthesis of this guanosine derivative was performed in analogy to that for the modified thymidine: A. Marx, P. Erdmann, M. Senn, S. Körner, T. Jungo, M. Petretta, P. Imwinkelried, A. Dussy, K. J. Kulicke, L. Macko, M. Zehnder, B. Giese, Helv. Chim. Acta 1996, 79, 1989. Photolysis of monomeric 4′-pivaloyl-substituted guanosine that was phosphorylated at the 3′-OH position gave the enol ether in 85% yield. This shows that the charge transfer between the carbohydrate radical cation and the base G is very fast.
28. 32P-labeled complementary strands. They were photolyzed for 15 min in phosphate buffer (200 μL, 20 mM, 100 mM NaCl, pH 7.0) at 15°C with a 500-W Hg high-pressure lamp in the absence of oxygen. An aliquot of the solution was incubated for 30 min with 1M piperidine at 90°C, then lyophilized overnight, and analyzed by denaturated polyacrylamide gel electrophoresis (1500 V, 3.5 h). The modified strands were replaced by unmodified strands in control experiments. The dried gels were autoradiographed with a phospho-imager and analyzed with the software ImageQuant. Quantification of the piperidine-induced bands was performed by substracting the intensities obtained in the control experiments from the intensities obtained with the modified double strands.
29. Experiments with other DNA strands are under way.
30. The measurements were carried out under the conditions described in detail in reference [4a]. The sequences of the strands correspond to those given there.