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A mechanism for the loss of 60 u from peptides containing an arginine residue at the C-terminus

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Journal of the American Society for Mass Spectrometry

Abstract

The loss of 60 u from protonated peptide ions containing an arginine residue at the C-terminus has been investigated by means of low energy tandem mass spectrometry. The lowest energy conformation of singly charged bradykinin is thought to involve a salt-bridge structure, which may lead to the formation of two isomeric forms. It is thought that one isomer retains the ionizing proton at the C-terminal end of the peptide, leading to the formation of the [b n−1 + H + OH]+ fragment ion, and the other isomer retains the charge at the N-terminus, leading to the formation of the [M + H − 60]+ fragment ion. It was found that the formation of the [M + H − 60]+ ion occurs only from singly charged precursor ions. In addition, the loss of 60 u occurs from peptides in which the charge is localized at the N-terminus. These results indicate that the mechanism of formation of the [M + H − 60]+ ion may be driven by a charge-remote process.

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References

  1. Hunt, D. F.; Yates, J. R. III; Shabanowitz, J.; Winston, S.; Hauer, C. R. Proc. Nat. Acad. Sci. USA 1986, 83, 6233–6237.

    Article  CAS  Google Scholar 

  2. Biemann, K.; Martin, S. A. Mass Spectrom. Rev. 1987, 6, 1–76.

    Article  CAS  Google Scholar 

  3. Biemann, K.; Scoble, H. A. Science 1987, 237, 992–998.

    Article  CAS  Google Scholar 

  4. Martin, S. A.; Biemann, K. Int. J. Mass Spectrom. Ion Processes 1987, 78, 213–228.

    Article  CAS  Google Scholar 

  5. Johnson, R. S.; Martin, S. A.; Biemann, K. Int. J. Mass Spectrom. Ion Processes 1988, 86, 137–154.

    Article  CAS  Google Scholar 

  6. Barinaga, C. J.; Edmonds, C. G.; Udseth, H. R. J.; Smith, R. D. Rapid Commun. Mass Spectrom. 1989, 3, 160–164.

    Article  CAS  Google Scholar 

  7. Smith, R. D.; Barinaga, C. J.; Udseth, H. R. J. Phys. Chem. 1989, 93, 5019–5022.

    Article  CAS  Google Scholar 

  8. Smith, R. D.; Loo, J. A.; Edmonds, C. G.; Barinaga, C. J.; Udseth, H. R. Anal. Chem. 1990, 62, 882–899.

    Article  CAS  Google Scholar 

  9. Loo, J. A.; Edmonds, C. G.; Smith, R. D. Anal Chem. 1993, 65, 425–438.

    Article  CAS  Google Scholar 

  10. Biemann, K. In Methods in Enzymology Vol. 193; McCloskey, J. A., Ed.; Academic: New York, 1990; pp 886–887.

    Google Scholar 

  11. Alexander, A. J.; Thibault, P.; Boyd, R. K.; Curtis, J. M.; Rinehart, K. L. Int. J. Mass Spectrom. Ion Processes 1990, 98, 107–134.

    Article  CAS  Google Scholar 

  12. Roepstorff, P.; Fohlman, J. Biomed. Mass Spectrom. 1984, 11, 601.

    Article  CAS  Google Scholar 

  13. Biemann, K. Biomed. Environ. Mass Spectrom. 1988, 16, 99–111.

    Article  CAS  Google Scholar 

  14. Mueller, D. R.; Eckersley, M.; Richter, W. J. Org. Mass Spectrom. 1988, 23, 217–222.

    Article  CAS  Google Scholar 

  15. Kenny, P. T.; Nomomto, K.; Orlando, R. Rapid Commun. Mass Spectrom. 1992, 6, 95–97.

    Article  CAS  Google Scholar 

  16. Cordero, M. M.; Houser, J. J.; Wesdemiotis, C. Anal. Chem. 1993, 65, 1594–1601.

    Article  CAS  Google Scholar 

  17. Arnott, D.; Kottmeier, D.; Yates, N.; Shabanowitz, J.; Hunt, D. F. Proceedings of the 42nd ASMS Conference on Mass Spectrometry and Allied Topics; Chicago, 1994; p 470.

  18. Yalcin, T.; Khouw, C.; Csizmadia, I. G.; Peterson, M. R.; Harrison, A. G. J. Am. Soc. Mass Spectrom. 1995, 6, 1165–1174.

    Article  CAS  Google Scholar 

  19. Renner, D.; Spiteller, G. Biomed. Environ. Mass Spectrom. 1988, 15, 75–77.

    Article  CAS  Google Scholar 

  20. Tang, X.; Ens, W.; Standing, K. G.; Westmore, J. B. Anal. Chem. 1988, 60, 1791–1799.

    Article  CAS  Google Scholar 

  21. Grese, R. P.; Cerny, R. L.; Gross, M. L. J. Am. Chem. Soc. 1989, 111, 2835–2842.

    Article  CAS  Google Scholar 

  22. Thorne, G. C.; Gaskell, S. J. Rapid Commun. Mass Spectrom. 1989, 3, 217.

    Article  CAS  Google Scholar 

  23. Thorne, G. C.; Ballard, K. D.; Gaskell, S. J. J. Am. Soc. Mass Spectrom. 1990, 1, 249–257.

    Article  CAS  Google Scholar 

  24. Teesch, L. M.; Orlando, R. C.; Adams, J. J. Am. Chem. Soc. 1991, 113, 3668–3675.

    Article  CAS  Google Scholar 

  25. Ballard, K. D.; Gaskell, S. J. J. Am. Chem. Soc. 1992, 114, 64–71.

    Article  CAS  Google Scholar 

  26. Tang, X.; Thibault, P.; Boyd, R. K. Org. Mass Spectrom. 1993, 28, 1047–1052.

    Article  CAS  Google Scholar 

  27. Gonzalez, J.; Besada, V.; Garay, H.; Reyes, O.; Padron, G.; Tambara, Y.; Takao, T.; Shimonishi, Y. J. Mass Spectrom. 1996, 31, 150–158.

    Article  CAS  Google Scholar 

  28. Teesch, L. M.; Adams, J. J. Am. Chem. Soc. 1990, 112, 4110–4120.

    Article  CAS  Google Scholar 

  29. Gross, M. L. Int. J. Mass Spectrom. Ion Processes 1992, 118, 137–165.

    Article  Google Scholar 

  30. Stults, J. T.; Lai, J.; McCune, S.; Wetzel, R. Anal. Chem. 1993, 65, 1703–1708.

    Article  CAS  Google Scholar 

  31. Schnier, P. D.; Price, W. D.; Jockusch, R. A.; Williams, E. R. J. Am. Chem. Soc. 1996, 18, 7178–7189.

    Article  Google Scholar 

  32. Cambell, S.; Rodgers, M. T.; Marzluff, E. M.; Beauchamp, J. L. J. Am. Chem. Soc. 1995, 117, 12840–12854.

    Article  Google Scholar 

  33. Cox, K. A.; Gaskell, S. J.; Moriis, M.; Whiting, A. J. Am. Soc. Mass Spectrom. 1996, 7, 522–531.

    Article  CAS  Google Scholar 

  34. Wyttenbach, T.; von Helden, G.; Bowers, M. T. J. Am. Chem. Soc. 1996, 18, 8355–8364.

    Article  Google Scholar 

  35. Teesch, L. M.; Adams, J. J. Am. Chem. Soc. 1991, 113, 812–820.

    Article  CAS  Google Scholar 

  36. Hu, P.; Gross, M. L. J. Am. Chem. Soc. 1992, 114, 9153–9160.

    Article  CAS  Google Scholar 

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Deery, M.J., Summerfield, S.G., Buzy, A. et al. A mechanism for the loss of 60 u from peptides containing an arginine residue at the C-terminus. J Am Soc Mass Spectrom 8, 253–261 (1997). https://doi.org/10.1016/S1044-0305(96)00197-3

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  • DOI: https://doi.org/10.1016/S1044-0305(96)00197-3

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