Oxidative Cleavage of a Cyclobutane Pyrimidine Dimer by Photochemically Generated Nitrate Radicals (NO3•)

Organic Letters

Volumn 3, Issue 10, 2001, Pages 1455-1458

  Krüger, Oliver ^a   Wille, Uta ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; NITRATE; PYRIMIDINE DIMER;

ARTICLE; DNA REPAIR; DRUG EFFECT; METABOLISM; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

DNA REPAIR; FREE RADICALS; NITRATES; OXIDATION-REDUCTION; PHOTOCHEMISTRY; PYRIMIDINE DIMERS;

EID: 0035902244     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0157252     Document Type: Article

References (33)

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8. Voityuk, A. A.; Michel-Beyerle, M.-E.; Rösch, N. J. Am. Chem. Soc. 1996, 118, 9750.
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11. (c) Dandliker, P. J.; Núńez, M. E.; Barton, J. K. Biochemistry 1998, 37, 6491.
12. Nitrate radicals are the most important oxidants in the nighttime atmosphere: Wayne, R. P.; Barnes, I.; Biggs, P.; Burrows, J. P.; Canosa-Mas, C. E.; Hjorth, J.; Le Bras, G.; Moortgat, G. K.; Perner, D.; Restelli, G.; Sidebottom, H. The Nitrate Radical: Physics, Chemistry and the Atmosphere, Wayne, R. P., Ed.; Atmos. Environ., Part A 1991, 25.
13. Wille, U.; Steenken, S., manuscript in preparation.
14. (a) Ito, T.; Shinohara, H.; Hatta, H.; Nishimoto, S.; Fujita, S. J. Phys. Chem. A 1999, 103, 8413.
15. (b) Heelis, P. F.; Deeble, D. J.; Kim, S.-T.; Sancar, A. Int. J. Radiat. Biol. 1992, 62, 137.
16. The dimers 1a-d were prepared in analogy to ref 2d and separated by column chromatography. The stereochemistry at the cyclobutane ring was assigned according to: Fahr, E.; Maul, P.; Lehner, K.-A.; Scheutzow, D. Z. Naturforsch. 1972, 27b, 1481.
17. Pac, C.; Kubo, J.; Majima, T.; Sakurai, H. Photochem. Photobiol. 1982, 36, 273.
18. (a) Lietzau, L.; Wille, U. Heterocycles 2001, 55, 377.
19. (b) Baciocchi, E.; Del Giacco, T.; Murgia, S. M.; Sebastiani, G. V. J. Chem. Soc., Chem. Commun. 1987, 1246 and literature cited therein.
20. -1.
21. The GC data given in Table 1 are relative peak areas determined without an internal standard. For each of the components in this investigation the response factor in the GC is approximately the same. In addition, it was verified by an independent experiment that the organic material could be quantitatively recovered after the irradiation and workup procedure (see ref 11).
22. It was verified that no photoinduced splitting of 1a-d occurred in the absence of CAN.
23. 3+: E° = 1.61 V vs NHE: Handbook of Chemistry and Physics, 63rd ed.; CRC Press, Boca Raton, Florida, 1995; D-162.
24. +], 193 (15), 164 (10), 136 (20), 108 (20), 82 (15), 42 (10).
25. The mechanism for formation of 7 is not clear. The one-electron reduction of 2 requires a potential of -2.11 V in MeCN: Scannell, M. P.; Prakash, G.; Falvey, D. E. J. Phys. Chem. A 1997, 101, 4332. Yet, we were not able to determine the reductive species in our system, as both Ce(III) and the nitrate ion could be strictly excluded.
26. Formation of compound 4 by photosensitized oxidative splitting from the syn uracil cyclobutane dimers 1a,b was reported in the literature: Elad, D.; Rosenthal, I.; Sasson, S. J. Chem. Soc. C 1971, 2053.
27. • with 10 also appeared but were not identified.
28. This may be important with respect to the fact that the T〈〉T lesions in DNA possess a cis-svn configuration at the cyclobutane ring. A preferred photochemical splitting of the syn configurated uracil cyclobutane dimers was described in ref 17. An analogous behavior was observed in splitting experiments using a photosensitizer and was explained by the lower oxidation potentials of the syn cyclobutane dimers: Rosenthal, I.; Rao, M. M.; Salomon, J. Biochem. Biophys. Acta 1975, 378, 165; and ref 9.
29. -: E° = 2.0 V vs SCE (in acetonitrile); see ref 10b.
30. • (not shown) may be suggested, is not clear. Pac et al. and Rosenthal et al. proposed (see refs 9 and 19) that a facile and selective splitting of the pyrimidine cyclobutane dimer may be achieved in a CT complex involving an intermediate with a partial positive charge developing on the pyrimidine dimer and a sensitizer, which acts as an electron acceptor. Therefore, the origin of the substrate selectivities should be due to steric effects. On the other hand, formation of the discrete radical cation of the dimer was found to lead to a rapid splitting independently of the structure at the cyclobutane ring.
31. Pouwels, P. J. W.; Hartman, R. F.; Rose, S. D.; Kaptein, R. Photochem. Photobiol. 1995, 61, 563.
32. • has been studied by us: Krüger, O.; Wille, U., manuscript in preparation. An analogous dealkylation of amines by anodic oxidation was reported in the literature: Kyriacou, D. Modern Electroorganic Chemistry; Springer- Verlag: Berlin, 1994.
33. • has been studied by us: Krüger, O.; Wille, U., manuscript in preparation. An analogous dealkylation of amines by anodic oxidation was reported in the literature: Kyriacou, D. Modern Electroorganic Chemistry; Springer-Verlag: Berlin, 1994.