Conformational analysis of the electron-transfer kinetics across oligoproline peptides using N,N-dimethyl-1,4-benzenediamine donors and pyrene-1-sulfonyl acceptors

Journal of Physical Chemistry B

Volumn 111, Issue 24, 2007, Pages 6878-6886

  Issa, Joseph B ^a   Salameh, Abdu S ^b   Castner Jr , Edward W ^a   Wishart, James F ^c   Isied, Stephan S ^a  

^a RUTGERS UNIVERSITY   (United States)

^b AMERICAN UNIVERSITY OF BEIRUT   (Lebanon)

^c BROOKHAVEN NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDES; PYRENE; SIGNAL ENCODING; STREAK CAMERAS;

ION DERIVATIVES; MULTIEXPONENTIAL KINETICS; PROLINE PEPTIDES;

ELECTRON TRANSITIONS;

EID: 84961983615     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp071599t     Document Type: Article

References (52)

1. Isied, S. S.; Vassilian, A.; Wishart, J. F.; Creutz, C.; Schwarz, H. A.; Sutin, N. J. Am. Chem. Soc. 1988, 110, 635-637.
2. Isied, S. S.; Ogawa, M. Y.; Wishart, J. F. Chem. Rev. 1992, 92, 381.
3. Ogawa, M. Y.; Moreira, I.; Wishart, J. F.; Isied, S. S. Chem. Phys. 1993, 176, 589.
4. (b) Ogawa, M. Y.; Wishart, J. F.; Young, Z.; Miller, J. R.; Isied, S. S. J. Phys. Chem. 1997, 97, 11456-11463.
5. Isied, S. S. In Principles of Electron-Transfer Reactions: Applications in Inorganic and Organometallic Chemistry and Biology; Isied, S. S., Ed.; Advances in Chemistry Series 253; American Chemical Society: Washington, DC, 1997.
6. Abdel Malak, R.; Gao, Z.; Wishart, J. F.; Isied, S. S. J. Am. Chem. Soc., 2004, 126, 13888-13889.
7. DeFelippis, M. R.; Faraggi, M.; Klapper, M. H. J. Am. Chem. Soc. 1990, 112, 5640.
8. (b) Chandrasekar, R.; Faraggi, M.; Klapper, M. H. J. Am. Chem. Soc. 1994, 116, 1414.
9. Bobrowski, K.; Holcman, J.; Poznanski, J.; Ciurak, M.; Wierzchowski, K. L. J. Phys. Chem. 1992, 96, 10036.
10. Jones, G., II; Lu, L. N.; Fu, H.; Farahat, C. W.; Oh, C.; Greenfield, S. R.; Gosztola, D. J.; Wasielewski, M. R. J. Phys. Chem. B 1999, 103, 572-581.
11. Meier, M. S.; Fox, M. A.; Miller, J. R. J. Org. Chem. 1991, 56, 5380-5384.
12. Cowan, P. M.; McGavin, S. Nature 1955, 176, 501-503.
13. Straub, W.; Shmueli, U. Nature 1963, 198, 1165-1166.
14. (a) Castner, E. W., Jr.; Kennedy, D.; Cave, R. J. J Phys. Chem. A 2000, 104, 2869-2885.
15. (b) Shirota, H.; Castner, E. W., Jr.; J. Chem. Phys. 2000, 112, 2367-2376.
16. (a) Shirota, H.; Castner, E. W., Jr.; Chem. Phys. 2000, 112, 2367-2376.
17. (b) Sun, Y.; Castner, E. W.; Lawson, C. L.; Falkowski, P. G. FEBS Lett. 2004, 570, 175-183.
18. (c) Grant, C. D.; DeRitter, M. R.; Steege, K. E.; Fadeeva, T. A.; Castner, E. W. Langmuir, 2005, 21, 1745-1752.
19. Becker, W. Advanced Time-Correlated Single Photon Counting Techniques: Springer Series in Chemical Physics; Springer: New York, Berlin, 2005.
20. Lakowicz, J. R. Principles of Fluorescence Spectroscope; Springer; New York, 2006; pp 140-141.
21. Ezzel, S. A.; McCormick, C. L. Macromolecules 1992, 25, 1881-1886.
22. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. CHARMM: A program for macromolecular energy, minimization, and dynamics calculations. J. Comput. Chem. 1983, 4, 187-217.
23. MacKerell, A. D., Jr.; Brooks, B.; Brooks, C. L., III; Nilsson, L.; Roux, B.; Won, Y.; Karplus, M. CHARMM: The Energy Function and Its Parameterization with an Overview of the Program. In The Encyclopedia of Computational Chemistry; Schleyer, P. V. R., et al., Eds.; John Wiley & Son: Chichester, 1998; Vol. 1, pp 271-277.
24. MacKerell, A. D., Jr.; Banavali, N.; Foloppe, N. Development and current status of the CHARMM force field for nucleic acids. Biopolymers 2001, 50, 257-265.
25. Becke, A. D. J. Chem. Phys. 1992, 96, 2155.
26. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
27. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1998, 37, 785.
28. Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, 117.
29. Cossi, M.; Barone, V. J. Chem. Phys. 2000, 112, 2427.
30. Cammi, R.; Mennucci, B.; Tomasi, J. J. Phys. Chem. A 2000, 104, 5631.
31. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
32. Cave, R. J.; Newton, M. D. Chem. Phys. Letters 1996, 249, 15-19.
33. Rust, M.; Lappe, J.; Cave, R. J. J. Phys. Chem. A 2002, 106, 3930-3940.
34. Thompson, Mark A. ArgusLab 4.0.1; Planaria Software LLC: Seattle, WA.
35. Bodanszky, M. Principles of Peptide Synthesis, 2nd ed.; Springer-Verlag; New York, 1993.
36. Petrov, E. G.; Shevchenko, Y. V.; Teslenko, V. I.; May, V. J. Chem. Phys. 2001, 115, 7107-7122.
37. Sneddon, S. F.; Brooks, C. L., III. J. Am. Chem. Soc. 1992, 114, 8220-8225.
38. Fischer, S.; Dunbrack, R. L, Jr..; Karplus, M. J. Am. Chem. Soc. 1994, 116, 11931-11937.
39. Zhong, H.; Carlson, H. A. J. Chem. Theory Comput. 2006, 2, 342-353.
40. Kang, Y. K.; Jhon, J. S.; Park, H. S. J. Phys. Chem. B 2006, 110, 17645-17655.
41. Sisido, M.; Tanaka, R.; Inai, Y.; Imanishi, Y. J. Am. Chem. Soc. 1989, 111, 6790.
42. Sasaki, H.; Makino, M.; Sisido, M.; Smith, T. A.; Ghiggino, K. P. J. Phys. Chem. B 2001, 105, 10416-10423.
43. Galoppini, E.; Fox, M. A. J. Am. Chem. Soc. 1996, 118, 2299-2300.
44. Fox, M. A.; Galoppini, E. J. Am. Chem. Soc. 1997, 119, 5277-5285.
45. (b) Knorr, A.; Galoppini, E.; Fox, M. A. J. Phys. Org. Chem. 1997, 10, 484-498.
46. Ogawa, M. Y. Mol. Supramol. Photochem. 1999, 4, 113-150.
47. Mutz, M. W.; McLendon, G. L.; Wishart, J. F.; Gaillard, E. R.; Corn, A. F. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 9521-9526.
48. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322.
49. Werner, U.; Wiessner, A.; Kuehnle, W.; Staerk, H. J. Photochem. Photobiol., A 1995, 85, 77-83.
50. (a) Jones, II, G.; Vullev, V. I. J. Phys. Chem. A 2001, 105, 6402-6406.
51. (b) Jones II, G.; Vullev, V. I. Org. Lett. 2001, 3, 2457-2460.
52. Schwarz, F. P.; Wasik, S. P. Anal. Chem. 1976, 48, 524-8.