The arginine anomaly: Arginine radicals are poor hydrogen atom donors in electron transfer induced dissociations

Journal of the American Chemical Society

Volumn 128, Issue 38, 2006, Pages 12520-12530

  Chen, Xiaohong ^a   Tureček, František ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; ELECTRON MOBILITY; HYDROGEN; MOLECULAR DYNAMICS; PHASE TRANSITIONS; POSITIVE IONS; PROBABILITY DENSITY FUNCTION;

ARGININE RADICALS; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSFER; REIONIZATION;

AMINO ACIDS;

2 AMINO 5 DIHYDROGUANID 1' YLPENTANAMIDE; AMIDE; ARGININE DERIVATIVE; GUANIDINE DERIVATIVE; HYDROGEN; RADICAL; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; AMINO ACID ANALYSIS; ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DENSITY FUNCTIONAL THEORY; DISSOCIATION; ELECTRON TRANSPORT; ENERGY; GAS;

ARGININE; ELECTRONS; FREE RADICALS; HYDROGEN; KINETICS; MASS SPECTROMETRY; MODELS, MOLECULAR; THERMODYNAMICS;

EID: 33749159528     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja063676o     Document Type: Article

References (83)

1. (a) Freiser, B. S.; Beauchamp, J. L. Chem. Phys. Lett. 1976, 42, 380-382.
2. (b) Freiser, B. S. Int. J. Mass Spectrom. Ion Phys. 1978, 26, 39-47.
3. (c) Cody, R. B.; Freiser, B. S. Anal. Chem. 1979, 51, 547-551.
4. Zubarev, R. A.; Kelleher, N. L.; McLafferty, F. W. J. Am. Chem. Soc. 1998, 120, 3265-3266.
5. Coon, J. J.; Ueberheide, B.; Syka, J. E. P.; Dryhurst, D. D.; Ausio, J.; Shabanowitz, J.; Hunt, D. F. Proc. Natl. Acad. Sci. USA. 2005, 102, 9463-9468.
6. (a) Zubarev, R. A.; Horn, D. M.; Fridriksson, E. K.; Kelleher, N. L.; Kruger, N. A.; Lewis, M. A.; Carpenter, B. K.; McLafferty, F. W. Anal. Chem. 2000, 72, 563-573.
7. (b) Zubarev, R. A. Mass Spectrom. Rev. 2003, 22, 57-77.
8. (c) Meng, F.; Forbes, A. J.; Miller, L. M.; Kelleher, N. L. Mass Spectrom. Rev. 2005, 24, 126-134.
9. (d) Cooper, H. J.; Hakansson, K.; Marshall, A. G. Mass Spectrom. Rev. 2005, 24, 201-222.
10. Yamashita, M.; Fenn, J. B. J. Phys. Chem. 1984, 88, 4451-4459.
11. Syrstad, E. A.; Tureček, F. J. Am. Soc. Mass Spectrom. 2005, 16, 208-224.
12. (a) Gatlin, C. L.; Tureček, F.; Vaisar, T. J. Am. Chem. Soc. 1995, 117, 3637-3638.
13. (b) Gatlin, C. L.; Rao, R. D.; Tureček, F.; Vaisar, T. Anal. Chem. 1996, 68, 263-270.
14. (c) Vaisar, T.; Gatlin, C. L.; Rao, R. D.; Seymour, J. L.; Tureček, F. J. Mass Spectrom. 2001, 36, 306-316.
15. Tureček, F.; Syrstad, E. A. J. Am. Chem. Soc. 2003, 125, 3353-3369.
16. Tureček, F. J. Am. Chem. Soc. 2003, 125, 5954-5963.
17. Bakken, V.; Helgaker, T.; Uggerud, E. Eur. J. Mass Spectrom. 2004, 10, 625-638.
18. Konishi, H.; Yokotake, Y.; Ishibashi, T. J. Mass Spectrom. Soc. Jpn. 2002, 50, 229-232.
19. Tureček, F.; Syrstad, E. A.; Seymour, J. L.; Chen, X.; Yao, C. J. Mass Spectrom. 2003, 38, 1093-1104.
20. O'Connor, P. B.; Lin, C.; Cournoyer, J. J.; Pittman, J. L.; Belyayev, M.; Budnik, B. A. J. Am. Soc. Mass Spectrom. 2006, 17, 576-585.
21. Leymarie, N.; Costello, C. E.; O'Connor, P. B. J. Am. Chem. Soc. 2003, 125, 8949-8958.
22. (a) Sobczyk, M.; Anusiewicz, I.; Berdys-Kochanska, J.; Sawicka, A.; Skurski, P.; Simons, J. J. Phys. Chem. A 2005, 109, 250-258.
23. (b) Anusiewicz, I.; Berdys-Kochanska, J.; Simons, J. J. Phys. Chem. A 2005, 109, 5801-5813.
24. (c) Anusiewicz, I.; Berdys-Kochanska, J.a; Skurski, P.; Simons, J. J. Phys. Chem. A 2006, 110, 1261-1266.
25. (d) Sobczyk, M.; Simons, J. J. Phys. Chem. B 2006, 110, 7519-7527.
26. Tureček, F. Top. Curr. Chem. 2003, 225, 77-129.
27. (a) Curtis, P. M.; Williams, B. W.; Porter, R. F. Chem. Phys. Lett. 1979, 65, 296-299.
28. (b) Burgers, P. C.; Holmes, J. L.; Mommers, A. A.; Terlouw, J. K. Chem. Phys. Lett. 1983, 102, 1-3.
29. (c) Danis, P. O.; Wesdemiotis, C.; McLafferty, F. W. J. Am. Chem. Soc. 1983, 105, 7454-7456.
30. For recent reviews, see: (a) Zagorevskii, D. V. In Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier: Oxford, 2004; pp 381-386.
31. (b) Tureček, F. In Encyclopedia of Mass Spectrometry; Armentrout, P. B., Ed.; Elsevier: Amsterdam, 2003; Vol. 1, Chapter 7, pp 528-541.
32. (c) Zagorevskii, D. V. Coord. Chem. Rev. 2002, 225, 5-34.
33. (d) Gerbaux, P.; Wentrup, C.; Flammang, R. Mass Spectrom. Rev. 2000, 19, 367-389.
34. (e) Zagorevskii, D. V.; Holmes, J. L. Mass Spectrom. Rev. 1999, 18, 87-118.
35. (f) Schalley, C.; Hornung, G.; Schröder, D. Schwarz, H. Chem. Soc. Rev. 1998, 27, 91-104.
36. Cooper, H. J. J. Am. Soc. Mass Spectrom. 2005, 16, 1932-1940.
37. Fung, Y. M. E.; Chan, T.-W. D. J. Am. Soc. Mass Spectrom. 2005, 16, 1523-1535.
38. (a) Tureček, F.; Gu, M.; Shaffer, S. A. J. Am. Soc. Mass Spectrom. 1992, 3, 493-501.
39. (b) Tureček, F. Org. Mass Spectrom. 1992, 27, 1087-1097.
40. Seymour, J. L.; Syrstad, E. A.; Langley, C. C.; Tureček, F. Int. J. Mass Spectrom. 2003, 228, 687-702.
41. Shaffer, S. A.; Tang, K.; Anderson, G. A.; Prior, D. C.; Udseth, H. R.; Smith, R. D. Rapid Commun. Mass Spectrom. 1997, 11, 1813-1817.
42. Frisch, M. J.; et al. Gaussian 03, revision B.05; Gaussian, Inc.; Pittsburgh, PA, 2003.
43. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377.
44. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
45. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627.
46. Dunning, T. H., Jr. J. Chem. Phys. 1989, 90, 1007-1023.
47. (a) Schlegel, H. B. J. Chem. Phys. 1986, 84, 4530-4534.
48. (b) Mayer, I. Adv. Quantum Chem. 1980, 12, 189-262.
49. Tureček, F. J. Phys. Chem. A 1998, 102, 4703-4713.
50. (a) Tureček, F.; Polásek, M.; Frank, A. J.; Sadílek, M. J. Am. Chem. Soc. 2000, 122, 2361-2370.
51. (b) Polásek, M.; Tureček, F. J. Am. Chem. Soc. 2000, 122, 9511-9524.
52. (c) Tureček, F.; Yao, C. J. Phys. Chem. A 2003, 107, 9221-9231.
53. (d) Rablen, P. R. J. Am. Chem. Soc. 2000, 122, 357-368.
54. (e) Rablen, P. R. J. Org. Chem. 2000, 65, 7930-7937.
55. (f) Rablen, P. R.; Bentrup, K. H. J. Am. Chem. Soc. 2003, 125, 2142-2147.
56. (g) Hirama, M.; Tokosumi, T.; Ishida, T.; Aihara, J. Chem. Phys. 2004, 305, 307-316.
57. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224.
58. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-745.
59. Gilbert, R. G.; Smith, S. C. Theory of Unimolecular and Recombination Reactions; Blackwell Scientific Publications: Oxford, 1990; pp 52-132.
60. Zhu, L.; Hase, W. L. Quantum Chemistry Program Exchange; Indiana University: Bloomington, 1994; Program No. QCPE 644.
61. Frank, A. J.; Sadílek, M.; Ferrier, J. G.; Tureček, F. J. Am. Chem. Soc. 1997, 119, 12343-12353.
62. Gdanitz, R. J.; Cardoen, W.; Windus, T. L.; Simons, J. J. Phys. Chem. A 2004, 108, 515-518.
63. NIST Standard Reference Database Number 69 - March, 2003 Release: http://webbook.nist.gov/chemistry.
64. (a) Carpenter, F. H.; Tureček, F. J. Chem. Soc., Perkin Trans. 2 1999, 2315-2323.
65. (b) Tureček, F.; Carpenter, F. H.; Polce, M. J.; Wesdemiotis, C. J. Am. Chem. Soc. 1999, 121, 7955-7956.
66. (c) O'Hair, R. A. J.; Blanksby, S.; Styles, M.; Bowie, J. H. Int. J. Mass Spectrom. 1999, 182/183, 203-211.
67. (d) Polce, M. J.; Wesdemiotis, C. J. Am. Soc. Mass Spectrom. 1999, 10, 1241-1247.
68. (a) Polce, M. J.; Wesdemiotis, C. J. Mass Spectrom. 2000, 35, 251-257.
69. (b) Tam, F.; Syrstad, E. A.; Chen, X.; Tureček, F. Eur. J. Mass Spectrom. 2004, 10, 869-880.
70. Amide enols such as the putative fragment 10 typically give very intense survivor ions in neutralization-reionization mass spectra (ref 16). The efficiencies in collisional reionization at keV kinetic energies scale with the number of atoms in the neutral molecule (ref 34) and should be comparable for 7 and 10 that differ by a single hydrogen atom.
71. Syrstad, E. A.; Stephens, D. D.; Tureček, F. J. Phys. Chem. A 2003, 107, 115-126.
72. (b) Chen, X.; Syrstad, E. A.; Tureček, F. J. Phys. Chem. A 2004, 108, 4163-4173.
73. Lifshitz, C. Mass Spectrom. Rev. 1982, 1, 309-348.
74. (a) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 1999, 103, 6268-6281.
75. (b) Wolken, J. K.; Tureček, F. J. Phys. Chem. A 2001, 105, 8352-8360.
76. (c) Tureček, F. Int. J. Mass Spectrom. 2003, 227, 327-338.
77. α-glycyl arginine show dissociations and rearrangements that are quite analogous to those in 1H. Tureček, F. Presented at the 54th ASMS Conference on Mass Spectrometry and Allied Topics, Seattle, May 28-June 2, 2006.
78. Cooper, H. J.; Hudgins, R. R.; Håkansson, K.; Marshall, A. G. J. Am. Soc. Mass Spectrom. 2002, 13, 241-249.
79. Cooper, H. J.; Hudsins, R. R.; Håkansson, K.; Marshall, A. G. Int. J. Mass Spectrom. 2003, 228, 723-728.
80. Iavarone, A. T.; Paech, K.; Williams, E. R. Anal. Chem. 2004, 78, 2231-2238.
81. Mihalca, R.; Kleinnijenhuis, A. J.; McDonnell, L. A.; Heck, A. J. R.; Heeren, R. M. A. J. Am. Soc. Mass Spectrom. 2004, 15, 1869-1873.
82. Polfer, N. C.; Haselmann, K. F.; Langridge-Smith, P. R. R.; Barran, P. E. Mol. Phys. 2005, 103, 1481-1489.
83. Patriksson, A.; Adams, C.; Kjeldsen, F.; Raber, J.; van der Spoel, D.; Zubarev, R. A. Int. J. Mass Spectrom. 2006, 248, 124-135.