Novel peptide dissociation: Gas-phase intramolecular rearrangement of internal amino acid residues

Journal of the American Chemical Society

Volumn 119, Issue 24, 1997, Pages 5481-5488

  Vachet, Richard W ^a   Bishop, Barney M ^a   Erickson, Bruce W ^a   Glish, Gary L ^a  

^a University of North Carolina at Chapel Hill   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AMINO ACID; ION; NITROGEN; PEPTIDE; PROTON;

AMINO TERMINAL SEQUENCE; ARTICLE; CHEMICAL MODIFICATION; CYCLOTRON; DISSOCIATION; FOURIER TRANSFORMATION; MASS SPECTROMETRY; MOLECULAR MODEL;

EID: 0030861687     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9640758     Document Type: Article

References (35)

1. Hunt, D. F.; Yates, J. R., III; Shabanowitz, J.; Winston, S.; Hauer, C. R. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 6233.
2. Biemann, K.; Martin, S. A. Mass Spectrom. Rev. 1987, 6, 1.
3. Carr, S. A.; Hemling, M. E.; Bean, M. F.; Roberts, G. D. Anal. Chem. 1991, 63, 2802.
4. Papayannopoulos, I. A. Mass Spectrom. Rev. 1995, 14, 49.
5. Tang, X.-J.; Thibault, P.; Boyd, R. K. Anal. Chem. 1993, 65, 2824.
6. Martin, S. A.; Biemann, K. Int. J. Mass Spectrom. Ion Processes 1987, 78, 213.
7. Johnson, R. S.; Martin, S. A.; Biemann, K.; Stults, J. T.; Watson, J. T. Anal. Chem. 1987, 59, 2621.
8. Johnson, R. S.; Martin, S. A.; Biemann, K. Int. J. Mass Spectrom. Ion Processes 1988, 86, 137.
9. Qin, J.; Chait, B. T. J. Am. Chem. Soc. 1995, 117, 5411.
10. Doroshenko, V. M.; Cotter, R. J. Anal. Chem. 1995, 67, 2180.
11. Vachet, R. W.; Asam, M. R.; Glish, G. L. J. Am. Chem. Soc. 1996, 118, 6252.
12. Van Berkel, G. J.; Glish, G. L.; McLuckey, S. A. Anal. Chem. 1990, 62, 1284.
13. Senko, M. W.; Hendrickson, C. L.; Paša-Tolić, L.; Marto, J. A.; White, F. M.; Guan, S.; Marshall, A. G. Rapid Commun. Mass Spectrom. 1996, 10, 1824.
14. Marshall, A. G.; Wang, T.-C. L.; Ricca, T. L. J. Am. Chem. Soc. 1985, 107, 7893.
15. Gauthier, J. W.; Trautman, T. R.; Jacobson, D. B. Anal. Chim. Acta 1991, 246, 211.
16. Bingham, R. C.; Dewar, M. J. S.; Lo, D. H. J. Am. Chem. Soc. 1975, 97, 1285.
17. Katakuse, I.; Desiderio, D. M. Int. J. Mass Spectrom. Ion Processes 1983, 54, 1.
18. Alexander, A. J.; Boyd, R. K. Int. J. Mass Spectrom. Ion Processes 1989, 90, 211.
19. Ballard, K. D.; Gaskell, S. J. Int. J. Mass Spectrom. Ion Processes 1991, 111, 173.
20. Thibault, P.; Alexander, A. J.; Boyd, R. K.; Tomer, K. B. J. Am. Soc. Mass Spectrom. 1993, 4, 845.
21. Yalcin, T.; Csizmadia, I. G.; Peterson, M. R.; Harrison, A. G. J. Am. Soc. Mass Spectrom. 1996, 7, 233.
22. The structure of the 34 ion is formally presumed to be an immonium ion in which the leucine residue on the C-terminus and the carbonyl group on the phenylalanine residue have been lost. The charge can formally be assigned to the nitrogen in the phenylalanine residue having four covalent bonds (pept-CO-NH=CHR).
23. Biemann, K. Biomed. Environ. Mass Spectrom. 1988, 16, 99.
24. Roepstorff, P.; Fohlman, J. Biomed. Mass Spectrom. 1984, 11, 601.
25. Arnott, D.; Kottmeier, D.; Yates, N.; Shabanowitz, J.; Hunt, D. F. Proceedings of the 42nd ASMS Conference on Mass Spectrometry and Allied Topics; Chicago, IL, 1994; p 470.
26. Tang, X. J.; Boyd, R. K. Rapid Commun. Mass Spectrom. 1994, 8, 578.
27. Wu, J.; Lebrilla, C. B. J. Am. Chem. Soc. 1993, 115, 3270.
28. Wu, J.; Gard, E.; Bregar, J.; Green, M. K.; Lebrilla, C. B. J. Am. Chem. Soc. 1995, 117, 9900.
29. Yalcin, T.; Khouw, C.; Csizmadia, I. G.; Peterson, M. R.; Harrison, A. G. J. Am. Soc. Mass Spectrom. 1995, 6, 1164.
30. Eckart, K. Mass Spectrom Rev. 1994, 13, 23.
31. At the pressures used in these experiments the ion at m/z 380 is expected to undergo on average about 0.01 collisions during one rf cycle. As a result it is unlikely that the ion at m/z 380 would dissociate to form m/z 323 as a result of collisional activation during the time when it is being resonantly ejected. It is also possible that m/z 380 could be formed from m/z 397 with sufficient excess internal energy to dissociate further to the ion at m/z 323 before it could be resonantly ejected. From a simple RRKM calculation, assuming a tight transition state and a critical energy of 1.2 eV, at least 5 eV of internal energy would be required to observe the dissociation of m/z 380 to m/z 323 in less than 1 μs. This amount of excess internal energy seems unlikely; therefore, it is reasonable to conclude that the double resonance experiments in this case are able to distinguish between a concerted reaction and two rapid consecutive reactions.
32. Mueller, D. R.; Eckersley, M.; Richter, W. J. Org. Mass Spectrom 1988, 23, 217.
33. Kenny, P. T. M.; Nomoto, K.; Orlando, R. Rapid Commun. Mass Spectrom. 1992, 6, 95.
34. Rozeboom, M. D.; Kiplinger, J. P.; Bartmess, J. E. J. Am. Chem. Soc. 1984, 106, 1025.
35. Eichinger, P. C. H.; Dua, S.; Bowie, J. H. Int. J. Mass Spectrom. Ion Processes 1994, 133, 1.