Electrochemical approach to the repair of oxetanes mimicking DNA (6-4) photoproducts

Journal of Physical Chemistry B

Volumn 110, Issue 43, 2006, Pages 21987-21993

  Boussicault, Fabien ^a   Robert, Marc ^a  

^a UNIVERSITÉ PARIS DIDEROT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMISTRY; ENZYMES; ESCHERICHIA COLI; IONS; OXIDATION; PARAFFINS; TRANSIENTS;

CARBON ELECTRODES; ELECTROCHEMICAL REDUCTION; OXETANES MIMICKING DNA; PHOTOPRODUCTS;

DNA;

EID: 33751296723     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp062425z     Document Type: Article

References (43)

1. (a) Neumann, A.; Scholz-Muramatsu, H.; Diekert, G. Arch. Microbiol 1994, 162, 295.
2. (b) Wohlfarth, G.; Diekert, G. Curr. Opin. Biotechnol. 1997, 8, 290.
3. Diekert, G.; Gugova, D.; Limoges, B.; Robert, M.; Savéant J.-M. J. Am. Chem. Soc. 2005, 127, 13583.
4. (a) Sancar, A. Chem. Rev. 2003, 103, 2203 and references therein.
5. (b) Taylor, J.-S. Acc. Chem. Res. 1994, 27, 76.
6. (c) Heelis, P. F.; Hartman, R. F.; Rose, S. D. Chem. Soc. Rev. 1995, 289.
7. (d) Carell, T.; Burgdorf, L. T.; Kundu, L. M.; Cichon, M. K. Curr. Opin. Chem. Biol. 2001 5, 491.
8. (e) Harrison, C. B.; O'Neil, L. L.; Wiest, O. J. Phys. Chem A 2005, 109, 7001.
9. (f) Kao, Y.-T.; Saxena, C.; Wang, L.; Sancar, A.; Zhong, D. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 16128.
10. Gibbs, P. E. M.; Kilbey, B. J.; Banerjee, S. K.; Lawrence, C. W. J. Bacteriol. 1993, 175, 2607.
11. (a) Todo, T.; Ryo, H. Mutat. Res. 1992, 273, 85.
12. (b) Kim, S.-T.; Malhotra, K.; Smith, C. A.; Taylor, J.-S.; Sancar, A. J. Biol. Chem. 1994, 209, 8535.
13. (c) Zhao, X.; Liu, J.; Hsu, D.; Zhao, S.; Taylor, J.-S.; Sancar, A. J. Biol. Chem. 1997, 272, 32580.
14. (d) Hitomi, K.; Kim, S.-T.; Iwai, S.; Harima, N.; Otoshi, E.; Ikenaga, M.; Todo, T. J. Biol. Chem. 1997, 272, 32591.
15. (e) Hitomi, K.; Nakamura, H.; Kim, S.-T.; Mizukoshi, T.; Ishikawa, T.; Iwai, S.; Todo, T. J. Biol. Chem. 2001, 276, 10103.
16. Mees, A.; Klar, T.; Gnau, P.; Hennecke, U.; Eker, A. P.; Carell, T.; Essen, L.-O. Science 2004, 306, 1789.
17. (a) Cichon, M. K.; Arnold, S.; Carell, T. Angew. Chem., Int. Ed. 2002, 41, 767.
18. (b) Friedel, M. O.; Cichon, M. K.; Carell, T. Org. Biomol. Chem. 2005, 3, 1937.
19. (c) Song, Q.-H.; Wang, H.-B.; Tang, W.-J.; Guo, Q.-X.; Yu, S.-Q. Org. Biomol. Chem. 2006, 4, 291.
20. (a) Wang, Y.; Gaspar, P. P.; Taylor, J.-S. J. Am. Chem. Soc. 2000, 122, 5510.
21. (b) Izquierdo, M. A.; Domingo, L. R.; Miranda, M. A. J. Phys. Chem. A 2005, 109, 2602.
22. (a) Prakash, G.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 11375.
23. (b) Joseph, A.; Prakash, G.; Falvey, D. E. J. Am. Chem. Soc. 2000, 122, 11219.
24. (c) Joseph, A.; Falvey, D. E. J. Am. Chem. Soc. 2001, 123, 3145.
25. Boussicault, F.; Krüger, O.; Robert, M.; Wille, U. Org. Biomol. Chem. 2004, 2, 2742.
26. Costentin, C.; Robert, M.; Savéant, J.-M. Chem. Phys. 2006, 324, 40 and references therein.
27. (a) Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2003, 125, 105.
28. (b) Costentin, C.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2004, 126, 16051.
29. 11
30. (a) Nadjo, L.; Savéant, J.-M. J. Electroanal. Chem. 1973, 48, 113.
31. substrate factors ranging from 1.13 to 1.18 in the application of eqs 1 and 2.
32. (a) See ref 15c for a full description of the fitting procedure.
33. s may be estimated to be 0.2 cm/s by comparison with molecules of similar size and charge.
34. (c) Pause, L.; Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2001, 123, 4886.
35. Boussicault, F.; Clivio, P.; Robert, M. Submitted for publication.
36. Kim, S.-T.; Sancar, A. Biochemistry 1991, 30, 8623.
37. 18b = -2.92 V vs SCE.
38. (b) Gindt, Y. M.; Schelvis, J. P. M.; Thoren, K. L.; Huang, T. H. J. Am. Chem. Soc. 2005, 127, 10472.
39. (a) Although not obtained from voltammetric study, the standard potentials for oxetanes 1-4 are likely slightly more negative than the reductive potentials measured at a low scan rate, -2.5 V vs SCE being an approximate but reasonable mean value. Moving to the real oxetane lesion and enzymatic environment should not move this value toward positive potentials by more than a few hundred millivolts.
40. (b) The driving force for back electron transfer is thus predicted to be more negative than -2 eV, while the reorganization energy A certainly does not exceed 1-1.5 eV.
41. Robert, M.; Savéant, J.-M. J. Am. Chem. Soc. 2000, 122, 514.
42. Garreau, D.; Savéant, J.-M. J. Electroanal. Chem. 1972, 35, 309.
43. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, M. A.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennuci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, G.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, A. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 98, Revision A.1; Gaussian, Inc.: Pittsburgh, PA, 1998.