Toward an Artificial Oxidative DNA Photolyase

Journal of Organic Chemistry

Volumn 69, Issue 2, 2004, Pages 543-548

  Pauvert, Mickaël ^a   Laine, Patrick ^a   Jonas, Marco ^a   Wiest, Olaf ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; DIMERS; DNA; HYDROGEN BONDS; POLYMERS; SYNTHESIS (CHEMICAL);

ASSOCIATION CONSTANT;

SUPRAMOLECULAR CHEMISTRY;

ANTHRAQUINONE; CYCLOBUTANE DERIVATIVE; CYCLOBUTANE PYRIMIDINE; DEOXYRIBODIPYRIMIDINE PHOTOLYASE; DIMER; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; DIMERIZATION; HYDROGEN BOND; ISOMER; MOLECULAR RECOGNITION; OXIDATION; POLARIZATION; SYNTHESIS;

CRYSTALLOGRAPHY, X-RAY; DEOXYRIBODIPYRIMIDINE PHOTO-LYASE; OXIDATIVE STRESS; PROTEIN BINDING;

EID: 0347132677     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0354600     Document Type: Article

References (63)

1. For monographs, see e.g.: (a) Friedberg, E. C. DNA Repair; W. H. Freeman & Co.: New York, 1985; Chapters 1-5, 2-1, and 2-2.
2. (b) Cadet, J.; Vigny, P. The Photochemistry of Nucleic Acids. In Bioorganic Photochemistry; Vol. I, Photochemistry and Nucleic Acids; Morrison, H., Ed.; Wiley & Sons: New York 1990; pp 53-100.
3. (c) Fischer, G. J.; Johns, H. E. Pyrimidine photodimers. In Photochemistry and Photobiology of Nucleic Acids; Wang, S. Y.;, Ed.; Academic Press: New York, 1976; Vol. I, pp 226-295.
4. (d) Patrick, M. H.; Rahn, R. O. Photochemistry of DNA and Polynucleotides: Photoproducts. In Photochemistry and Photobiology of Nucleic Acids; Wang, S. Y.; Ed.; Academic Press: New York, 1976; Vol. I, pp 35-95.
5. (a) Taylor, J.-S. Pure Appl. Chem. 1995, 67, 183-190.
6. (b) Taylor, J.-S. Acc. Chem. Res. 1994, 27, 76-82.
7. (a) Begley, T. P. Compr. Nat. Prod. Chem. 1999, 5, 371-399.
8. (b) Sancar, A. Chem. Rev. 2003, 103, 2203-2238.
9. (c) Heelis, P. F.; Hartman, R. F.; Rose, S. D. Chem. Soc. Rev. 1995, 24, 289-297.
10. (a) Goodman, M. S.; Rose, S. D. J. Org. Chem. 1992, 57, 3268-3270.
11. (b) Harzfeld, D. G.; Rose, S. D. J. Am. Chem. Soc. 1993, 115, 850-854.
12. (c) Carell, T.; Epple, R.; Gramlich, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 620-623.
13. (d) Epple, R.; Carell, T. J. Am. Chem. Soc. 1999, 121, 7318-7329.
14. (e) Carell, T.; Burgdorf, L.; Butenandt, J.; Epple, R.; Schwogler, A. In Bioorganic Chemistry; Diederichsen, U., Ed.; Wiley-VCH: New York, 1999; pp 337-345.
15. (a) Dervan, P. B. Bioorg., Med. Chem. 2001, 9, 2215-2235.
16. (b) Deans, R.; Niemz, A.; Breinlinger, E. C.; Rotello, V. R. J. Am. Chem. Soc. 1997, 119, 10863-10864.
17. (a) Sessler, J. L.; Wang, R. J. Org. Chem. 1998, 63, 4079-4091.
18. (b) Sessler, J. L.; Wang, R. Angew. Chem., Int. Ed. 1998, 37, 1726-1729.
19. Tecilla, P.; Jubian, V.; Hamilton, A. D. Tetrahedron 1995, 51, 435-448.
20. Park, T. K.; Schroder, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1991, 113, 5125-5127.
21. It is possible that the cis,syn derivative has in fact a higher association constant than the reported value because the procedure used for the synthesis of the CPD derivative used was later shown to yield the trans,syn derivative: (b) Cochran, A. G.; Sugasawara, R.; Schultz, P. G. J. Am. Chem. Soc. 1988, 110, 7888-7890.
22. (c) Jacobsen J. R.; Cochran, A. G.; Stephans, J. C.; King, D. S.; Schultz, P. G J. Am. Chem. Soc. 1995, 117, 5453-5461.
23. (a) Hirst, S. C.; Hamilton, A. D. Tetrahedron Lett. 1990, 31, 2401-2404.
24. (b) Hamilton, A. D.; Little, D. J. Chem. Soc., Chem. Commun. 1990, 297-300.
25. (c) Hamilton, D. A.; VanEngen, D. J. Am. Chem. Soc. 1987, 109, 5035-5036.
26. (a) Goodman, M. S.; Rose, S. D. J. Org. Chem. 1992, 57, 3268-3270.
27. (b) Van Camp, J. R.; Young, T.; Hartman, R. F.; Rose, S. D. Photochem. Photobiol. 1987, 45, 365-370.
28. (c) Kim, S. T.; Young, T.; Goodman, M. S.; Forrest, C.; Hartman, R. F.; Rose, S. D. Trends Photochem. Photobiol. 1990, 1, 81-87.
29. Takase, M.; Inouye, M. J. Org. Chem. 2003, 68, 1134-1137.
30. Inouye, M.; Takase, M. Angew. Chem., Int. Ed. 2001, 40, 1746-1748.
31. Inouye, M.; Hyodo, Y.; Nakazumi, H. J. Org. Chem. 1999, 64, 2704-2710.
32. Murty, K. V. S. N.; Vasella, A. Helv. Chim. Acta 2001, 84, 939-963.
33. Katz, H. E. J. Org. Chem. 1989, 54, 2179-2183.
34. Pouwels, P. J. W.; Hartman, R. F.; Rose, S. D.; Kaptein, R. Photochem. Photobiol. 1995, 61, 563-574.
35. Sasson, S.; Elad, D. J. Org. Chem. 1972, 37, 3164-3167.
36. Pryor, K. E.; Shipps, G. W.; Skyler, D. A.; Rebek, J., Jr. Tetrahedron 1998, 54, 4107-4124.
37. Nettekoven, M. Synlett 2001, 12, 1917-1919.
38. Nettekoven, M.; Jenny, C. Org. Proc. Res. Dev. 2003, 7, 38-43.
39. Yao, Y.; Lamba, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1998, 120, 2805-2810.
40. Vögtle, F.; Koch, H.; Rissanen, K. Chem. Ber. 1992, 125, 2129-35.
41. Lampe, B. Chem. Ber. 1909, 42, 1413-1418.
42. For recent publications, compare e.g.: (a) Liao, Y.; Fathi, R.; Yang, Z. Org. Lett. 2003, 5, 909-912.
43. (b) Russell, J. M.; Sabat, M.; Grimes, R. N. Organometallics 2002, 21, 4113-4128.
44. (c) Zhao, Y.; McDonald, R.; Tykwinski, R. R. J. Org. Chem. 2002, 67, 2805-2812.
45. Crisp, G. T.; Turner, P. D.; Stephens, K. A. J. Organomet. Chem. 1998, 570, 219-224.
46. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017.
47. Inbasekaran, M.; Witiak, D. T. J. Med. Chem. 1980, 23, 278-281.
48. This is also in agreement with our observation that addition of veratrole to a solution of 12 in hot DMF inhibits the normally observed crystallization upon cooling.
49. Würthner, F.; Yao, S.; Beginn, U. Angew. Chem., Intl. Ed. 2003, 42, 3247-3250.
50. (b) Ishada, Y.; Aida, T. J. Am. Chem. Soc. 2002, 124, 14017-14019.
51. Calculated at the B3LYP/6-31G* level of theory, using the coordinates from the X-ray structure
52. E.g.: (a) Curtin, D. Y.; Paul, I. C. Chem. Rev. 1981, 81, 525-541.
53. (b) Evan, O. R.; Lin, W. Acc. Chem. Res. 2002, 35, 511-522.
54. (a) Jouaiti, A.; Hosseini, M. W.; Kyritsakas, N. Chem. Commun. 2002, 1898-1899.
55. For an example of a purely organic material, compare: (b) Martz, J.; Graf, E.; Hosseini, M. W.; DeCian, A.; Fischer, J. J. Chem. Soc., Dalton Trans. 2000, 3791-3795.
56. (a) Marder, S. R.; Sohn, J. E.; Stucky, G. D. Materials for Nonlinear Optics; ACS Symp. Ser. 445; American Chemical Society: Washington, DC, 1991.
57. (b) uNonlinear Optical Properties of Organic Molecules and Crystals; Chemla, D. S., Zyss, J., Eds.; Academic Press: New York, 1987; Vols. 1 and 2.
58. For examples of two-component complexes with hydrogen bonding in aromatic compounds, compare also: Muthuraman, M.; Masse, R.; Nicoud, J.-F.; Desiraju, G. R. Chem. Mater. 2001, 13, 1473-1479.
59. Foster, R.; Fyfe, C. A. Prog. Nucl. Magn. Reson. Spectrosc. 1969, 4, 1-89.
60. -1.
61. Kondo, S.; Utsumi, K.; Yano, Y. Internet J. Sci.: Biol. Chem. [Electronic Publication] 1997, 1, http://www.netsci-journal.com/97v1/ 97012/index.htm.
62. Carell, T.; Epple, R.; Gramlich, V. Helv. Chim. Acta 1997, 80, 2191-2203.
63. Benesi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703-2707.