Pentafluorophenyl-phenyl interactions in biphenyl-DNA

Chemistry - A European Journal

Volumn 11, Issue 7, 2005, Pages 2125-2129

  Zahn, Alain ^a   Brotschi, Christine ^a   Leumann, Christian J ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

Biphenyl derivatives; Fluoroarenes; Isothermal titration calorimetry; Oligonucleotides; Stacking interactions

Indexed keywords

AROMATIC COMPOUNDS; CALORIMETRY; DERIVATIVES; HYDROPHOBICITY; MELTING; OLIGOMERS; TITRATION;

BIPHENYL DERIVATIVES; FLUOROARENES; ISOTHERMAL TITRATION CALORIMETRY; OLIGONUCLEOTIDES; STACKING INTERACTIONS;

DNA;

BENZENE DERIVATIVE; BIPHENYL DERIVATIVE; DNA; FLUORINE DERIVATIVE; NUCLEOTIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CALORIMETRY; DEHYDRATION; ENTHALPY; FLUORINATION; MELTING POINT; MOLECULAR INTERACTION; SOLVATION; THERMODYNAMICS; THERMOSTABILITY; ULTRAVIOLET RADIATION;

BIPHENYL COMPOUNDS; CALORIMETRY; CIRCULAR DICHROISM; DNA; MOLECULAR CONFORMATION; OLIGONUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; SENSITIVITY AND SPECIFICITY; TEMPERATURE; TITRIMETRY;

EID: 15944412838     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200401128     Document Type: Article

References (60)

1. C. R. Cantor, P. R. Schimmel, Biophysical Chemistry Part III: The Behavior of Biological Macromolecules, Vol. 2 (Ed.: P. C. Vapnek), W. H. Freeman & Co., New York, 1980, pp. 1109-1181.
2. W. Saenger, Principles of Nucleic Acid Structure, Springer, New York, 1984.
3. B. A. Schweitzer, E. T. Kool, J. Am. Chem. Soc. 1995, 117, 1863-1872.
4. K. M. Guckian, J. C. Morales, E. T. Kool, J. Org. Chem. 1998, 63, 9652-9656.
5. [S] T. J. Matray, E. T. Kool, J. Am. Chem. Soc. 1998, 120, 6191-6192.
6. B. M. O'Neill, J. E. Ratto, K. L. Good, D. C. Tahmassebi, S. A. Helquist, J. C. Morales, E. T. Kool, J. Org. Chem. 2002, 67, 5869-5875.
7. J. C. Morales, E. T. Kool, Nat. Struct. Biol. 1998, 5, 950-954.
8. S. Moran, R. X.-F. Ren, E. T. Kool, Proc. Natl. Acad. Sci. USA 1997, 94, 10 506-10 511.
9. D. L. McMinn, A. K. Ogawa, Y. Wu, J. Liu, P. G. Schultz, F. E. Romesberg, J. Am. Chem. Soc. 1999, 121, 11 585-11 586.
10. M. Berger, A. K. Ogawa, D. L. McMinn, Y. Wu, P. G. Schultz, F. E. Romesberg, Angew. Chem. 2000, 112, 3069-3071; Angew. Chem. Int. Ed. 2000, 39, 2940-2942.
11. M. Berger, A. K. Ogawa, D. L. McMinn, Y. Wu, P. G. Schultz, F. E. Romesberg, Angew. Chem. 2000, 112, 3069-3071; Angew. Chem. Int. Ed. 2000, 39, 2940-2942.
12. A. K. Ogawa, Y. Wu, D. L. McMinn, J. Liu, P. G. Schultz, F. E. Romesberg, J. Am. Chem. Soc. 2000, 122, 3274-3287.
13. E. L. Tae, Y. Wu, G. Xia, P. G. Schultz, F. E. Romesberg, J. Am. Chem. Soc. 2001, 123, 7439-7440.
14. M. Berger, S. D. Luzzi, A. A. Henry, F. E. Romesberg, J. Am. Chem. Soc. 2002, 124, 1222-1226.
15. C. Yu, A. Henry, F. E. Romesberg, P. G. Schultz, Angew. Chem. 2002, 114, 3997-4000; Angew. Chem. Int. Ed. 2002, 41, 3841-3844.
16. C. Yu, A. Henry, F. E. Romesberg, P. G. Schultz, Angew. Chem. 2002, 114, 3997-4000; Angew. Chem. Int. Ed. 2002, 41, 3841-3844.
17. E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244-1287; Angew. Chem. Int. Ed. 2003, 42, 1210-1250.
18. E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem. 2003, 115, 1244-1287; Angew. Chem. Int. Ed. 2003, 42, 1210-1250.
19. M. R. Battaglia, A. D. Buckingham, J. H. Williams, Chem. Phys. Lett. 1981, 78, 421-423.
20. C. R. Patrick, G. S. Prosser, Nature, 1960, 187, 1021.
21. J. H. Williams, J. K. Cockcroft, A. N. Fitch, Angew. Chem. 1992, 104, 1666-1669; Angew. Chem. Int. Ed. Engl. 1992, 31, 1655-1657.
22. J. H. Williams, J. K. Cockcroft, A. N. Fitch, Angew. Chem. 1992, 104, 1666-1669; Angew. Chem. Int. Ed. Engl. 1992, 31, 1655-1657.
23. J. H. Williams, Acc. Chem. Res. 1993, 26, 593-598.
24. C. A. Hunter, Angew. Chem. 1993, 105, 1653-1655; Angew. Chem. Int. Ed. Engl. 1993, 32, 1584-1586.
25. C. A. Hunter, Angew. Chem. 1993, 105, 1653-1655; Angew. Chem. Int. Ed. Engl. 1993, 32, 1584-1586.
26. C. A. Hunter, X.-J. Lu, J. Chem. Soc. Faraday Trans. 1995, 91, 2009-2015.
27. a) F. Cozzi, M. Cinquini, R. Annuziata, J. S. Siegel, J. Am. Chem. Soc. 1993, 115, 5330-5331;
28. b) F. Cozzi, F. Ponzini, R. Annuziata, M. Cinquini, J. S. Siegel, Angew. Chem. 1995, 107, 1092-1094; Angew. Chem. Int. Ed. Engl. 1995, 34, 1019-1020;
29. b) F. Cozzi, F. Ponzini, R. Annuziata, M. Cinquini, J. S. Siegel, Angew. Chem. 1995, 107, 1092-1094; Angew. Chem. Int. Ed. Engl. 1995, 34, 1019-1020;
30. c) F. Cozzi, J. S. Siegel, Pure Appl. Chem. 1995, 67, 683-689.
31. N. M. D. Brown, F. L. Swinton, J. Chem. Soc. Chem. Commun. 1974, 770-771.
32. V. E. Williams, R. P. Lemieux, G. R. J. Thatcher, J. Org. Chem. 1996, 61, 1927-1933.
33. G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty, R. H. Grubbs, Angew. Chem. 1997, 109, 290-293; Angew. Chem. Int. Ed. Engl. 1997, 36, 248-251.
34. G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty, R. H. Grubbs, Angew. Chem. 1997, 109, 290-293; Angew. Chem. Int. Ed. Engl. 1997, 36, 248-251.
35. F. Ponzini, R. Zagha, K. Hardcastle, J. S. Siegel, Angew. Chem. 2000, 112, 2413-2415; Angew. Chem. Int. Ed. 2000, 39, 2323-2325.
36. F. Ponzini, R. Zagha, K. Hardcastle, J. S. Siegel, Angew. Chem. 2000, 112, 2413-2415; Angew. Chem. Int. Ed. 2000, 39, 2323-2325.
37. T. Liu, H.-J. Schneider, Angew. Chem. 2002, 114, 1418-1420; Angew. Chem. Int. Ed. 2002, 41, 1368-1370.
38. T. Liu, H.-J. Schneider, Angew. Chem. 2002, 114, 1418-1420; Angew. Chem. Int. Ed. 2002, 41, 1368-1370.
39. G. Mathis, J. Hunziker, Angew. Chem. 2002, 114, 3335-3338; Angew. Chem. Int. Ed. 2002, 41, 3203-3205.
40. G. Mathis, J. Hunziker, Angew. Chem. 2002, 114, 3335-3338; Angew. Chem. Int. Ed. 2002, 41, 3203-3205.
41. K. A. Frey, S. A. Woski, Chem. Commun. 2002, 2206-2207.
42. a) J. Parsch, J. W. Engels, Helv. Chim. Acta 2000, 83, 1791-1808;
43. b) J. Parsch, J. W. Engels, J. Am. Chem. Soc. 2002, 124, 5664-5672.
44. J. S. Lai, J. Qu, E. T. Kool, Angew. Chem. 2003, 115, 6155-6159; Angew. Chem. Int. Ed. 2003, 42, 5973-5977.
45. J. S. Lai, J. Qu, E. T. Kool, Angew. Chem. 2003, 115, 6155-6159; Angew. Chem. Int. Ed. 2003, 42, 5973-5977.
46. J. S. Lai, E. T. Kool, J. Am. Chem. Soc. 2004, 126, 3040-3041.
47. C. Brotschi, A. Haeberli, C. J. Leumann, Angew. Chem. 2001, 113, 3101-3103; Angew. Chem. Int. Ed. 2001, 40, 3012-3014.
48. C. Brotschi, A. Haeberli, C. J. Leumann, Angew. Chem. 2001, 113, 3101-3103; Angew. Chem. Int. Ed. 2001, 40, 3012-3014.
49. C. Brotschi, C. J. Leumann, Angew. Chem. 2003, 115, 1694-1697; Angew. Chem. Int. Ed. 2003, 42, 1655-1658.
50. C. Brotschi, C. J. Leumann, Angew. Chem. 2003, 115, 1694-1697; Angew. Chem. Int. Ed. 2003, 42, 1655-1658.
51. C. Brotschi, G. Mathis, C. J. Leumann, Chem. Eur. J. 2005, in press.
52. W. Timpe, K. Dax, N. Wolf, H. Weidmann, Carbohydr. Res. 1975, 39, 53-60.
53. P. J. N. Brown, M. T. Chaudhry, R. Stephens, J. Chem. Soc. C 1969, 2747-2750.
54. G. A. Kraus, M. T. Molina, J. Org. Chem. 1988, 53, 752-753.
55. K. Krohn, H. Heins, K. Wielckens, J. Med. Chem. 1992, 35, 511-517.
56. a) K. M. Guckian, B. A. Schweitzer, R. X.-F. Ren, C. J. Sheils, P. L. Paris, D. C. Tahmassebi, E. T. Kool, J. Am. Chem. Soc. 1996, 118, 8182-8183;
57. b) K. M. Guckian, R. X.-F. Ren, N. C. Chaudhuri, D. T. Tahmassebi, E. T. Kool, J. Am. Chem. Soc. 2000, 122, 2213-2222.
58. F. Grein, J. Phys. Chem. A, 2002, 106, 3823-3827.
59. C. P. Brock, D. G. Naae, N. Goodhand, T. A. Hamor, Acta Crystallogr. 1978, B34, 3691-3696.
60. H. Adams, J.-L. Jimenez-Blanco, G. Chessari, C. A. Hunter, C. M. R. Low, J. M. Sanderson, J. G. Vinter, Chem. Eur. J. 2001, 7, 3494-3503.