Sugar conformational effects on the photochemistry of thymidylyl(3′-5′)thymidine

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6502-6510

  Ostrowski, Tomasz ^a   Maurizot, Jean Claude ^b   Adeline, Marie Thérèse ^a   Fourrey, Jean Louis ^a   Clivio, Pascale ^a  

^a CNRS   (France)

^b CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; DIMERS; PHOTOLYSIS; SYNTHESIS (CHEMICAL);

BASE-STACKED CONFORMATIONS;

SUGARS;

2' O,5 DIMETHYL 3',5' URIDYLYL 2' O,5 DIMETHYLURIDINE; CYCLOBUTANE DERIVATIVE; HYDROGEN; PYRIMIDINE DIMER; SUGAR; THYMIDINE DERIVATIVE; THYMIDYLYL 3',5' THYMIDINE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATION; GEOMETRY; PHOTOLYSIS; SYNTHESIS;

CARBOHYDRATE CONFORMATION; CIRCULAR DICHROISM; DEOXYRIBOSE; DINUCLEOSIDE PHOSPHATES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PHOTOCHEMISTRY;

EID: 0043011175     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030086p     Document Type: Article

References (60)

1. (a) Cadet, J.; Vigny, P. In Bioorganic Photochemistry: The Photochemistry of Nucleic Acids; Morrison, H., Ed.; Wiley: New York, 1990; Vol. 1, pp 1-272.
2. (a) Cleaver, J. E.; Crowley, E. Front. Biosci. 2002, 7, d1024-1043.
3. (b) Ullrich, S. E. Front. Biosci. 2002, 7, d684-703.
4. (a) Matsunaga, T.; Hieda, K.; Nikaido, O. Photochem. Photobiol. 1991, 54, 403-410.
5. (b) Sage, E. Photochem. Photobiol. 1993, 57, 163-174.
6. (c) Pfeifer, G. P. Photochem. Photobiol. 1997, 65, 270-283.
7. (d) Perdiz, D.; Grof, P.; Mezzina, M.; Nikaido, O.; Moustacchi, E.; Sage, E. J. Biol. Chem. 2000, 275, 26732-26742.
8. (e) Liu, X.; Conconi, A.; Smerdon, M. J. Biochemistry 1997, 36, 13710-13717.
9. (f) Aboussekhra, A.; Thoma, F. EMBO J. 1999, 18, 433-443.
10. (g) Ghosh, R.; Paniker, L.; Mitchell, D. L. Photochem. Photobiol. 2001, 73, 1-5.
11. (h) Wang, Y.; Gross, M. L.; Taylor, J.-S. Biochemistry 2001, 40, 11785-11793.
12. Clivio, P.; Guillaume, D. Tetrahedron Lett. 1998, 39, 6881-6884.
13. Thomas, M.; Clivio, P.; Guillaume, D.; Fourrey, J.-L. Nucleosides Nucleotides Nucleic Acids 2001, 20, 927-929.
14. Lesnik, E. A.; Freier, S. M. Biochemistry 1998, 37, 6991-6997 and references therein.
15. Lee, C.-H.; Ezra, F. S.; Kondo, N. S.; Sarma, R. H.; Danyluk, S. S. Biochemistry 1976, 15, 3627-3638.
16. Cheng, D. M.; Sarma, R. H. J. Am. Chem. Soc. 1977, 99, 7333-7348.
17. (a) Cheng, D. M.; Sarma, R. H, Biopolymers 1977, 16, 1687-1711.
18. (b) Kawai, G.; Yamamoto, Y.; Kamimura, T.; Masegi, T.; Sekine, M.; Hata, T.; Iimori, T.; Watanabe, T.; Miyazawa, T.; Yokoyama, S. Biochemistry 1992, 31, 1040-1046.
19. (a) Ohtsuka, E.; Inoue, H. Japanese Patent 02 264 792, 1990; Chem. Abstr. 1991, 114, 164721j.
20. (b) Martin, P. Helv. Chim. Acta 1995, 78, 486-504.
21. Chanteloup, L.; Thuong, N. T. Tetrahedron Lett. 1994, 35, 877-880.
22. Lewis, A. F.; Revankar, G. R.; Hogan, M. E. J. Heterocycl. Chem. 1993, 30, 1309-1315.
23. Ross, B. S.; Springer, R. H.; Tortorici, Z.; Dimock, S. Nucleosides Nucleotides 1997, 16, 1641-1643.
24. McGee, D. P. C.; Zhai, Y. Nucleosides Nucleotides 1996, 15, 1797-1803.
25. Jones, S. S.; Reese, C. B.; Ubasawa, A. Synthesis 1982, 259-260.
26. Fraser, A.; Wheeler, P.; Dan Cook, P.; Sanghvi, Y. S. J. Heterocycl. Chem. 1993, 30, 1277-1287.
27. McGee, D. P. C.; Vargeese, C.; Zhai, Y.; Kirschenheuter, G. P.; Settle, A.; Siedem, C. R.; Pieken, W. A. Nucleosides Nucleotides 1995, 14, 1329-1339.
28. Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333-2344.
29. Davies, D. B.; Danyluk, S. S. Biochemistry 1974, 13, 4417-4434.
30. Peeling, J.; Hruska, F. E.; Loewen, P. C. Can. J. Chem. 1978, 56, 522-529.
31. Guschlbauer, W.; Jankowski, K. Nucleic Acids Res. 1980, 8, 1421-1433.
32. Plavec, J.; Tong, W.; Chattopadhyaya, J. J. Am. Chem. Soc. 1993, 115, 9734-9746.
33. Rycyna, R. E.; Alderfer, J. L. Nucleic Acids Res. 1985, 13, 5949-5963.
34. Koning, T. M. G.; van Soest, J. J. G.; Kaptein, R. Eur. J. Biochem. 1991, 195, 29-40.
35. Johns, H. E.; Pearson, M. L.; LeBlanc, J. C.; Helleiner, C. W. J. Mol. Biol. 1964, 9, 503-524.
36. 4). An independent analysis of the separate photolysis of 1a and 1b resolved without ambiguity the origin of each photoproduct.
37. Drake, A. F.; Mason, S. F.; Trim, A. R. J. Mol. Biol. 1974, 86, 727-739.
38. Cantor, C. R.; Warshaw, M. M.; Shapiro, H. Biopolymers 1970, 9, 1059-1077.
39. Warshaw, M. M.; Cantor, C. R. Biopolymers 1970, 9, 1079-1103.
40. Brahms, J.; Maurizot, J. C.; Michelson, A. M. J. Mol. Biol. 1967, 25, 481-495.
41. Rabczenko, A.; Shugar, D. Acta Biochim. Pol. 1971, 18, 387-402.
42. Norberg, J.; Nilsson, L. Biophys. J. 1995, 69, 2277-2285.
43. Saenger, W. In Principles of Nucleic Acid Structure; Cantor, C. R., Ed.; Springer-Verlag: New York, 1984.
44. Malathi, R.; Yathindra, N. J. Biomol. Struct. Dyn. 1985, 3, 127-144 and references therein.
45. Norberg, J.; Nilsson, L. J. Am. Chem. Soc. 1995, 117, 10832-10840.
46. Malathi, R.; Yathindra, N. Int. J. Biol. Macromol. 1982, 4, 18-24.
47. Yathindra, N.; Sundaralingam, M. Biopolymers 1979, 18, 2721-2731.
48. Turro, N. J. In Molecular Photochemistry; Breslow, R., Karplus, M., Eds. ; W. A. Benjamin: New York, 1967.
49. Ruzsicska, B. P.; Lemaire, D. G. E. In CRC Handbook of Organic Photochemistry and Photobiology; Horspool, W. M., Song, P.-S., Eds.; CRC Press: Boca Raton, FL, 1995; pp 1289-1317.
50. (a) Hosszu, J. L.; Rahn, R. O. Biochem. Biophys. Res. Commun. 1967, 29, 327-330.
51. (b) Wacker, A.; Lodemann, E. Angew. Chem. 1965, 77, 133.
52. (c) Tramer, Z.; Wierzchowski, K. L.; Shugar, D. Acta Biochim. Pol. 1969, 16, 83-107.
53. Santini, G. P. H.; Cognet, J. A. H.; Clivio, P. Unpublished results.
54. Patrick, M. H.; Rahn, R. O. In Photochemistry and Photobiology of Nucleic Acids: Photochemistry of DNA and Polynucleotides: Photoproducts; Wang, S. Y., Ed.; Academic Press: New York, 1976; Vol. 2, pp 35-95.
55. (a) Mohr, S. C.; Sokolov, N. V. H. A.; He, C.; Setlow, P. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 77-81.
56. (b) Nicholson, W. L.; Setlow, B.; Setlow, P. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 8288-8292.
57. Douki, T.; Court, M.; Cadet, J. J. Photochem. Photobiol. B: Biol. 2000, 54, 145-154.
58. (a) Rahn, R. O.; Hosszu, J. L. Biochim. Biophys. Acta 1969, 190, 126-131.
59. (b) Patrick, M. H.; Gray, D. M. Photochem. Photobiol. 1976, 24, 507-513.
60. Sober, H. A. CRC Handbook of Biochemistry; Sober, H. A., Ed.; CRC Press: Cleveland, OH, 1968; p G-50.