Intramolecular Interaction between Nitroxide Radical and Photoexcited Benzophenone Triplet Linked to Peptide Templates

Journal of Physical Chemistry A

Volumn 107, Issue 36, 2003, Pages 6905-6912

  Sartori, E ^a   Toffoletti, A ^a   Rastrelli, F ^a   Corvaja, C ^a   Bettio, A ^a   Formaggio, F ^a   Oancea, S ^a   Toniolo, C ^a  

^a UNIVERSITY OF PADOVA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

INTRAMOLECULAR INTERACTIONS;

AMINO ACIDS; LASER PULSES; LIGHT ABSORPTION; MOLECULAR DYNAMICS; POLYPEPTIDES; REACTION KINETICS;

FREE RADICALS;

EID: 0142007247     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0345203     Document Type: Article

References (60)

1. Porter, G.; Wright, M. R. Discuss. Faraday Soc. 1959, 27, 18.
2. (a) Hoytink, G. J. Mol. Phys. 1969, 2, 114.
3. (b) Razi Naqvi, K.; Staerk, H.; Gillbro, T. Chem. Phys. Lett. 1977, 49, 160.
4. Ziegler, J.; Karl, N. Chem. Phys. 1979, 40, 207.
5. (a) Blättler, C.; Jent, F.; Paul, H. Chem. Phys. Lett. 1990, 166, 375.
6. (b) Kawai, A.; Okutsu, T.; Obi, K. J. Phys. Chem. 1991, 95, 9130.
7. (c) Kawai, A.; Obi, K. J. Phys. Chem. 1992, 96, 5701.
8. (a) Shushin, A. I. Zeit. Physik. Chem. 1993, 182, 9.
9. (b) Goudsmit, G.-H.; Paul, H.; Shushin, A. I. J. Phys. Chem. 1993, 97, 13243.
10. de Kanter, F. J. J.; den Hollander, J. A.; Huizer, A. H.; Kaptein, R. Mol. Phys. 1977, 34, 857.
11. Turro, N. J.; Koptyug, I. V.; van Willigen, H.; McLauchlan, K. A. J. Magn. Reson. A 1994, 109, 121.
12. (a) Corvaja, C.; Maggini, M.; Prato, M.; Scorrano, G.; Venzin, M. J. Am. Chem. Soc. 1995, 117, 8857.
13. (b) Corvaja, C.; Maggini, M.; Ruzzi, M.; Scorrano, G.; Toffoletti, A. Appl. Magn. Reson. 1997, 12,4 77.
14. (c) Ishi, K.; Fujisawa, J.; Ohba, Y.; Yamauchi, S. J. Am. Chem. Soc. 1996, 118, 13079.
15. (d) Jockusch, S.; Dedola, G.; Lem, G.; Turro, N. J. J. Phys. Chem. B 1999, 103, 9126.
16. (e) Corvaja, C.; Sartori, E.; Toffoletti, A.; Formaggio, F.; Crisma, M.; Toniolo, C.; Mazaleyrat, J.-P.; Wakselman, M. Chem. Eur. J. 2000, 6, 2775.
17. In the case of a rigid connection, J is constant, and the time dependent perturbation responsible for quartet doublet transitions is the electron spin dipolar interaction, modulated by the molecular tumbling motion.
18. (a) Forbes, M. D. E.; Bhagat, K. J. J. Am. Chem. Soc. 1993, 115, 3382.
19. (b) Forbes, M. D. E.; Ruberu, S. R. J. J. Phys. Chem. 1993, 97, 13223.
20. (c) Forbes, M. D. E. J. Am. Chem. Soc. 1993, 115, 1613.
21. (d) Avdievich, N. I.; Forbes, M. D. E. J. Phys. Chem. 1995, 99, 9660.
22. Toniolo, C.; Crisma, M.; Formaggio, F. Biopolymers (Pept. Sci.) 1998, 47, 153.
23. Kauer, J. C.; Erickson-Viitanen, S.; Wolfe, H. R. J.; DeGrado, W. F. J. Biol. Chem. 1986, 261, 10695.
24. Toniolo, C.; Benedetti, E. Trends Biochem. Sci. 1991, 16, 350.
25. (a) Auvin-Guette, C.; Rebuffat, S.; Prigent, Y.; Bodo, B. J. Am. Chem. Soc. 1992, 114, 2170.
26. (b) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C.; Monaco, V.; Goulard, C.; Rebuffat, S.; Bodo, B. J. Am. Chem. Soc., 1996, 118, 4952.
27. (c) Monaco, V.; Formaggio, F.; Crisma, M.; Toniolo, C.; Hanson, P.; Millhauser, G. L. Biopolymers 1999, 50, 239.
28. (a) Toniolo, C.; Benedetti, E. Macromolecules 1991, 24, 4004.
29. (b) Karle, I. L.; Balaram, P. Biochemistry 1990, 29, 6747.
30. (c) Karle, I. L. Acc. Chem. Res. 1999, 32, 693.
31. (d) Toniolo, C.; Crisma, M.; Formaggio, F.; Peggion, C. Biopolymers (Pept. Sci.) 2001, 60, 396.
32. (a) Rassat, A.; Rey, P. Bull. Chem. Soc. Fr. 1967, 815.
33. (b) Dulog, L.; Wang, W. Liebigs Ann. Chem. 1992, 301.
34. (c) Smythe, M. L.; Nakaie, C. R.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 10555.
35. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397.
36. (a) Jones, D. S.; Kenner, G. W.; Preston, J.; Sheppard, R. C. J. Chem. Soc. 1965, 6227.
37. (b) Benedetti, E.; Bavoso, A.; Di Blasio, B.; Pavone, V.; Pedone, C.; Crisma, M.; Bonora, G. M.; Toniolo, C. J. Am. Chem. Soc. 1982, 104, 2437.
38. Hanson, P.; Millhauser, G.; Formaggio, F.; Crisma, M.; Toniolo, C. J. Am. Chem. Soc. 1996, 118, 7618.
39. Moroder, L.; Hallett, A.; Wünsch, E.; Keller, O.; Wersin, G. Hoppe Seyler's Z. Physiol. Chem. 1976, 357, 1651.
40. Hyperchem, Hypercube, Inc., Gainesville, FL.
41. Bui, T. T. T.; Formaggio, F.; Crisma, M.; Monaco, V.; Toniolo, C.; Hussain, R.; Siligardi, G. J. Chem. Soc., Perkin Trans. 2000, 2, 1043.
42. (a) Mizushima, S.; Shimanouchi, T.; Tsuboi, M.; Souda, R. J. Am. Chem. Soc. 1952, 74, 270.
43. (b) Palumbo, M.; Da Rin, S.; Bonora, G. M.; Toniolo, C. Makromol. Chem. 1976, 177, 1477.
44. Toniolo, C.; Bonora, G. M.; Barone, V.; Bavoso, A.; Benedetti, E.; Di Blasio, B.; Grimaldi, P.; Lelj, F.; Pavone, V.; Pedone, C. Macromolecules 1985, 18, 895.
45. Kennedy, D. F.; Crisma, M.; Toniolo, C.; Chapman, D. Biochemistry 1991, 30, 6541.
46. Toniolo, C.; Peggion, C.; Crisma, M.; Formaggio, F.; Shui, X.; Eggleston, D. S. Nature: Struct. Biol. 1994, 1, 908.
47. (a) Crisma, M.; Monaco, V.; Formaggio, F.; Toniolo, C.; George, C.; Flippen-Anderson, J. L. Lett. Pept. Sci. 1997, 4, 213.
48. (b) Monaco, V.; Formaggio, F.; Crisma, M.; Toniolo, C.; Hanson, P.; Millhauser, G.; George, C.; Deschamps, J. R.; Flippen-Anderson, J. L. Bioorg. Med. Chem. 1999, 7, 119.
49. Goudsmith, G. H.; Paul, H. Chem. Phys. Lett. 1993, 208, 73.
50. (a) Percival, P. W.; Hyde, J. S. J. Magn. Reson. 1976, 23, 249.
51. (b) Hwang, J. S.; Mason, R. P.; Hwang, L. P.; Freed, J. H. J. Phys. Chem. 1975, 79, 489.
52. -1) is high enough not to appreciably influence the measured rate constants.
53. Corvaja, C.; Sartori, E.; Toffoletti, A.; Formaggio, F.; Crisma, M.; Toniolo, C. Biopolymers 2000, 55, 486.
54. I = -1.
55. The triplet benzophenone decay time in acetonitrile at room temperature is 50 μs (Wallace, W. L.; Van Duyne, R. P.; Lewis, F. D. J. Am. Chem. Soc. 1976, 98, 5319).
56. Kobori, Y.; Takeda, K.; Tsuji, K.; Kawai, A.; Obi, K. J. Phys. Chem. A 1998, 102, 5160.
57. 373 cP at 290 K (Yaws, C. L. In Handbook of Viscosity; Gulf Publishing Company: Houston, TX, 1995; Vol. 1, p 327).
58. The spectrum of the I mM 5 and benzophenone mixture was not used for the simulations and the kinetic discussion because of its very low signal-to-noise ratio (∼2).
59. -1 were chosen for distance calculations.
60. -1 when both peptides were 5 mM, thus showing a concentration dependence stronger than in all other cases. An intermolecular hydrogen abstraction could explain this behaviour.