Mechanism and energetics of intramolecular hydrogen transfer in amide and peptide radicals and cation-radicals

Journal of the American Chemical Society

Volumn 125, Issue 11, 2003, Pages 3353-3369

  Tureček, František ^a   Syrstad, Erik A ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENERGETICS;

AMMONIA; ELECTRON TUNNELING; ELECTRONS; POLYPEPTIDES; PROTONS;

ENERGY TRANSFER;

AMIDE; AMMONIA; AMMONIUM DERIVATIVE; CARBONYL DERIVATIVE; CATION; PEPTIDE; RADICAL;

ARTICLE; CALCULATION; CHEMICAL BOND; ELECTRON; ELECTRON TRANSPORT; ELECTRONICS; ENERGY; EXPERIMENTAL MODEL; PHASE TRANSITION; PROTON TRANSPORT; QUANTUM MECHANICS; QUANTUM THEORY; REACTION ANALYSIS;

ALANINE; AMIDES; CATIONS; FREE RADICALS; GLYCYLGLYCINE; HYDROGEN; MODELS, CHEMICAL; MODELS, MOLECULAR; PEPTIDES; THERMODYNAMICS;

EID: 0038756506     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja021162t     Document Type: Article

References (77)

1. Hawkins, C. L.; Davies, M. J. Biochim. Biophys. Acta 2001, 1504, 196-219.
2. Sun, X.; Harder, J.; Krook, M.; Jornvall, H.; Sjoberg, B. M.; Reichard, P. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 577-581.
3. Mulliez, E.; Fontecave, M.; Gaillard, J.; Reichard, P. J. Biol. Chem. 1993, 268, 2296-2299.
4. Sun, X.; Eliasson, R.; Pontis, E.; Andersson, J.; Buist, G.; Sjoberg, B. M.; Reichard, P. J. Biol. Chem. 1995, 270, 2443-2446. For a review, see: Jordan, A.; Reichard, P. Annu. Rev. Biochem. 1998, 67, 71-98.
5. Sun, X.; Eliasson, R.; Pontis, E.; Andersson, J.; Buist, G.; Sjoberg, B. M.; Reichard, P. J. Biol. Chem. 1995, 270, 2443-2446. For a review, see: Jordan, A.; Reichard, P. Annu. Rev. Biochem. 1998, 67, 71-98.
6. Knappe, J.; Neugebauer, F. A.; Blaschkowski, H. P.; Ganzler, M. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 1332-1335.
7. Parast, C. V.; Wong, K. K.; Lewisch, S. A.; Kozarich, J. W.; Peisach, J.; Magliozzo, R. S. Biochemistry 1995, 34, 2393-2399.
8. (a) Zubarev, R. A.; Kelleher, N. L.; McLafferty, F. W. J. Am. Chem. Soc. 1998. 120, 3265-3266.
9. (b) Kruger, N. A.; Zubarev, R. A.; Carpenter, B. K.; Kelleher, N. L.; Horn, D. M.; McLafferty, F. W. Int. J. Mass Spectrom. 1999, 182/183, 1-5.
10. Zubarev, R. A.; Kruger, N. A.; Fridriksson, E. K.; Lewis, M. A.; Horn, D. M.; Carpenter, B. K.; McLafferty, F. W. J. Am. Chem. Soc. 1999, 121, 2857-2862.
11. Perkins, C. W.; Martin, J. C.; Arduengo, A. J.; Lau, W.; Alegria, A.; Kochi, J. K. J. Am. Chem. Soc. 1980, 102, 7753.
12. For peptide fragment nomenclature, see: (a) Roepstorff, P.; Fohlman, J. Biomed. Mass Spectrom. 1984, 11, 601. (b) Biemann, K. Biomed. Environ. Mass Specrrom. 1988, 16, 99.
13. For peptide fragment nomenclature, see: (a) Roepstorff, P.; Fohlman, J. Biomed. Mass Spectrom. 1984, 11, 601. (b) Biemann, K. Biomed. Environ. Mass Spectrom. 1988, 16, 99.
14. Polfer, N. C.; Haselmann, K. F.; Zubarev, R. S. A.; Langridge-Smith, P. R. R. Rapid Commun. Mass Spectrom. 2002, 16, 936-943.
15. Breuker, K.; Oh, H. B.; Cerda, B. A.; Horn, D. M.; McLafferty, F. W. Eur. Mass Spectrom. 2002, 8, 177-180.
16. Shaffer, S. A.; Sadílek, M.; Tureček, F.; Hop, C. E. C. A. Int. J. Mass Spectrom. Ion Processes 1997, 160, 137-155.
17. Shaffer, S. A.; Wolken, J. K.; Tureček, F J. Am. Soc. Mass Spectrom. 1997, 8, 1111-1123.
18. Syrstad, E. A.; Turecek, F. J. Phys. Chem. A 2001, 105, 11144-11155.
19. Syrstad, E. A.; Stephens, D. D.; Turecek, F. J. Phys. Chem. A 2003, 107, 115-126.
20. Hudgins, R. R.; Hakansson, K.; Quinn, J. P.; Hendrickson, C. L.; Marshall, A. G. Proceedings of the 50th Annual Conference on Mass Spectrometry and Allied Topics; Orlando, FL, June 2002.
21. Shaffer, S. A.; Sadílek, M.; Tureček, F. J. Org. Chem. 1996, 61, 5234-5245.
22. Cooper, H. J.; Hudgins, R. R.; Hakansson, K.; Marshall, A. G. J. Am. Soc. Mass Spectrom. 2002, 13, 241-249.
23. Tureček, F. Proceedings of the 50th Annual Conference on Mass Spectrometry and Allied Topics; Orlando, FL, June 2002.
24. Konishi, H.; Yokotake, Y.; Ishibashi, T. J. Mass Spectrom Soc. Jpn. 2002, 50, 229-232.
25. Siegbahn, P. E. M.; Blomberg, M. R. A.; Crabtree, R. H. Theor. Chim. Acc. 1997, 97, 289-300.
26. Siegbahn, P. E. M.; Eriksson, L.; Himo, F.; Pavlov, M. J. Phys. Chem. B 1998, 102, 10622-10629.
27. Cujier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369.
28. Mayer, J. M.; Hrovat, D. A.; Thomas, J. L.; Borden, W. T. J. Am. Chem. Soc. 002, 124, 11142-11147.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.6; Gaussian, Inc.: Pittsburgh, PA, 1998.
30. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372, 5648.
31. (b) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623.
32. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618-622.
33. Schlegel, H. B. J. Chem. Phys. 1986, 84, 4530-4534.
34. Tureček, F. J. Phys. Chem. A 1998, 102, 4703-4713.
35. Rablen, P. R. J. Am. Chem. Soc. 2000, 122, 357-368.
36. (a) Wolken, J. K.; Tureček, F. J. Am. Chem. Soc. 1999, 121, 6010-6018.
37. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 1999, 103, 6268-6281.
38. (c) Tureček, F.; Polášek, M.; Frank, A. J.; Sadílek, M. J. Am. Chem. Soc. 2000, 122, 2361-2370.
39. (d) Polášek, M.; Tureček F. J. Am. Chem. Soc. 2000, 122, 9511-9524.
40. (e) Wolken, J. K.; Tureček, F. J. Am. Soc. Mass Spectrom. 2000, 11, 1065-1071.
41. (f) Tureček, F. J. Mass Spectrom. 2000, 35, 1351-1359.
42. (g) Wolken, J. K.; Syrstad, E. A.; Vivekananda, S.; Tureček, F. J. Am. Chem. Soc. 2001, 123, 5804-5805.
43. (h) Vivekananda, S.; Tureček, F.; Polášek, M. J. Mass Spectrom. 2002, 37, 829-839.
44. (i) Tureček, F.; Vivekananda, S.; Sadilek, M.; Polášek, M. J. Am. Chem. Soc. 2002, 124, 13282-13289.
45. Rassolov, V. A.; Ratner, M. A.; Pople, J. A. J. Chem. Phys. 2000, 112, 4014-4019.
46. Pople, J. A.; Head-Gordon, M.; Raghavachari, K. J. Chem. Phys. 1987, 87, 5968-5975.
47. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224.
48. Levine, I. N. Physical Chemistry, 3rd ed.; McGraw-Hill: New York, 1988; p 846.
49. (a) Gellene, G. I.; Porter, R. F. Acc. Chem. Res. 1983, 16, 200-207.
50. (b) Williams, B. W.; Porter, R. F. J. Chem. Phys. 1980, 73, 5598-5604.
51. (c) Gellene, G. I.; Cleary, D. A.; Porter, R. F. J. Chem. Phys. 1982, 77, 3471-3477.
52. (d) Boldyrev, A. I.; Simons, J. J. Chem. Phys. 1992, 97, 6621-6627.
53. (e) Nguyen, V. Q.; Sadílek, M.; Frank, A. J.; Ferrier, J. G.; Tureček, F. J. Phys. Chem. A 1997, 101, 3789-3799.
54. (f) Shaffer, S. A.; Tureček, F. J. Am. Chem. Soc. 1994, 116, 8647-8653.
55. (g) Frøsig, L.; Tureček, F. J. Am. Soc. Mass Spectrom. 1998, 9, 242-254.
56. (h) Sadílek, M.; Tureček, F. J. Phys. Chem. 1996, 100, 9610-9614.
57. Paisz, B.; Suhai, S. Rapid Commun. Mass Spectrom, 2001, 15, 2307-2323.
58. Yu, D.; Rauk, A.; Armstrong, D. A. J. Am. Chem. Soc. 1995, 117, 1789-1796.
59. Bonifacic, M.; Stefanic, I.; Hug, G. L.; Armstrong, D. A.; Asmus, K.-D. J. Am. Chem. Soc. 1998, 120, 9930-9940.
60. Tureček, F.; Carpenter, F. H.; Polce, M. J.; Wesdemiotis, C. J. Am. Chem. Soc. 1999, 121, 7955-7956.
61. Ban, F.; Wetmore, S. D.; Boyd, R. J. J. Phys. Chem. A 1999, 103, 4303-4308.
62. Carpenter, F. H.; Tureček, F. J. Chem. Soc., Perkin Trans. 2 1999, 2315-2323.
63. Tureček, F.; Reid, P. J. Int. J. Mass Spectrom. 2003, 222, 49-61.
64. Tureček, F. Org. Mass Spectrom. 1991, 26, 1074-1081.
65. Price, W. D.; Schnier, P. D.; Jockusch, R. A.; Strittmatter, E. F.; Williams, E. R. J. Am. Chem. Soc. 1996, 118, 10640-10644.
66. Bell, R. P. The Tunnel Effect in Chemistry; Chapman and Hall: London, 1980; p 27.
67. Fernandez-Ramos, A.; Truhlar, D. G. J. Chem. Phys. 2001, 114, 1491-1496.
68. Truhlar, D. G.; Kuppermann, A. J. Am. Chem. Soc. 1971, 93, 1840-1851.
69. Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, 5523-5527.
70. Eckart, C. Phys. Rev. 1930, 35, 1303.
71. Carpenter, B. K. J. Am. Chem. Soc. 1983, 105, 1700-1701.
72. -1 by G2, ref 16).
73. Estrup, P. J.; Wolfgang, R. J. Am, Chem. Soc. 1960, 82, 2665-2669.
74. Keizer, J. J. Chem. Phys. 1973, 58, 4524-4535. For a review, see: Gaspar, P. P.; Root, J. W. Radiochim. Acta 1981, 28, 191-213.
75. Keizer, J. J. Chem. Phys. 1973, 58, 4524-4535. For a review, see: Gaspar, P. P.; Root, J. W. Radiochim. Acta 1981, 28, 191-213.
76. (a) Bohme, D. K.; Mackay, G. I.; Schiff, H. I. J. Chem. Phys. 1980, 73, 4976-4986.
77. (b) Lias, S. G.; Shold, D. M.; Ausloos, P. J. Am. Chem. Soc. 1980, 102, 2540-2548.