Gas-phase fragmentation of protonated mono-N-methylated peptides. Analogy with solution-phase acid-catalyzed hydrolysis

Journal of Mass Spectrometry

Volumn 33, Issue 6, 1998, Pages 505-524

  Vaisar, Tomáš ^a   Urban, Jan ^a  

^a Molecumetics Ltd   (United States)

Author keywords

Collision induced dissociation; Fragmentation mechanism; N methylated peptides; Protonated oxazolone

Indexed keywords

AMINO ACID; PEPTIDE FRAGMENT; PROLINE;

ALKYLATION; ARTICLE; HYDROLYSIS; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTON TRANSPORT;

EID: 0031837553     PISSN: 10765174     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1096-9888(199806)33:6<505::AID-JMS662>3.0.CO;2-1     Document Type: Article

References (49)

1. (a) W. Braun, J. Kallen, V. Mikol, M. D. Walkinshaw and K. Wuthrich, FASEB J. 9, 63 (1995);
2. (b) D. Seebach, A. Studer and E. Pfammatter, Helv. Chim. Acta 77, 2035 (1994);
3. (c) N. Fusetani and S. Matsunaga, Chem. Rev. 93, 1793 (1993);
4. (d) G. Muller, M. Gurrath, M. Kurz and H. Kessler, Proteins: Struct. Funct. Genet. 15, 235 (1993).
5. M. Barber, R. J. Bordoli, R. D. Sedgwick and A. N. Tyler, Nature (London) 293, 270 (1981).
6. E. Lederer, Pure Appl. Chem. 17, 489 (1968);
7. (b) W. O. Godtfredsen, S. Vangedal and D. W. Thomas, Tetrahedron 26, 4931 (1970);
8. (c) T. J. Yu, H. Schwartz, R. W. Giese, B. L. Karger and P. Vouros, J. Chromatogr. 218, 519 (1981);
9. (d) K. Rose, A. Bairoch and R. E. Offord, J. Chromatogr. 268, 197 (1983).
10. K. Eckart, H. Schwarz, M. Chrev and C. Gilon, Eur. J. Biochem. 157, 209 (1986).
11. K. Eckart, personal communication.
12. (a) B. L. Schwartz and M. M. Bursey, Biol. Mass Spectrom. 21, 92 (1992);
13. (b) J. A. Loo, C. G. Edmonds and R. D. Smith, Anal. Chem. 65, 425 (1993).
14. T. Vaisar and J. Urban, J. Mass Spectrom. 31, 1185 (1996).
15. D. F. Hunt, J. R. Yates, III, J. Shabanowitz, S. Winston and C. R. Hauer, Proc. Natl. Acad. Sci. USA 83, 6233 (1986).
16. (a) D. R. Mueller, M. Eckersley and W. J. Richter, Org. Mass Spectrom. 23, 217 (1988);
17. (b) P. T. M. Kenny, K. Nomoto and R. Orlando, Rapid Commun. Mass Spectrom. 6, 95 (1992).
18. (a) A. L. McCormack, A. Somogyi, A. R. Dongre and V. H. Wysocki, Anal. Chem. 65, 2859 (1993);
19. (b) A. Somogyi, V. H. Wysocki and I. Mayer, J. Am. Soc. Mass Spectrom. 5, 704 (1994).
20. S. Scheiner and L. Wang, J. Am. Chem. Soc. 115, 1958 (1993).
21. D. Arnott, D. Kottmeier, N. Yates, J. Shabanowitz and D. Hunt, in Proceedings of the 42nd ASMS Conference on Mass Spectrometry and Allied Topics, Chicago, IL, 1994, p. 470.
22. (a) T. Yalcin, C. Khouw, I. G. Csizmadia, M. R. Peterson and A. G. Harrison, J. Am. Soc. Mass Spectrom. 6, 1164 (1995);
23. (b) M. J. Nold, C. Wesdemiotis, T. Yalcin, and A. G. Harrison, Int. J. Mass Spectrom. Ion Processes 164, 137 (1997).
24. K. Eckart, M. C. Holthausen, T. Brauningen, W. Koch and J. Spiess, in Proceedings of the 43rd ASMS Conference on Mass Spectrometry and Allied Topics, Atlanta, GA, 1995, p. 1046.
25. S. G. Summerfield, M. S. Bolgar and S. J. Gaskell, J. Mass Spectrom. 32, 225 (1997).
26. J. L. Jones, A. R. Dongre, A. Somogyi and V. H. Wysocki, J. Am. Chem. Soc. 116, 8368 (1994).
27. A. R. Dongre, J. L. Jones, A. Somogyi and V. H. Wysocki, J. Am. Chem. Soc. 118, 8365 (1996).
28. A. R. Dongre, A. Somogyi and V. H. Wysocki, J. Mass Spectrom. 31, 339 (1996).
29. (a) K. Zhang, C. J. Cassady, and, A. Chung-Phillips, J. Am. Chem. Soc. 116, 11512 (1994);
30. (b) J. Wu and C. B. Lebrilla, J. Am. Soc. Mass Spectrom. 6, 91 (1995).
31. (a) J. Wu and C. B. Lebrilla, J. Am. Chem. Soc. 115, 3270 (1993);
32. (b) K. Zhang, D. M. Zimmerman, A. Chung-Phillips and C. J. Cassady, J. Am. Chem. Soc. 115, 10812 (1993).
33. R. S. Johnson, D. Krylov and K. A. Walsh, J. Mass Spectrom. 30, 386 (1995).
34. M. Przybylski, I. Dietrich, I. Manz and H. Bruckner, Biomed. Mass Spectrom. 11, 569 (1984).
35. J. Urban, T. Vaisar, R. Shen and M. S. Lee, Int. J. Pept. Protein Res. 47, 182 (1996).
36. E. P. Hunter and S. G. Lias, in NIST Standard Reference Database No. 69, edited by. W. G. Mallard and P. J. Linstrom, National Institute of Standards and Technology, Gaithersburg, MD (1997) (http://webbook.nist.gov).
37. T. Vaisar and J. Urban, in Proceedings 43rd ASMS Conference on Mass Spectrometry and Allied Topics, Atlanta, GA, 1995, p. 631.
38. A. S. Kolaskar and K. P. Sarathy, Biopolymers 19, 1345 (1980).
39. D. K. Chalmers and G. R. Marshall, J. Am. Chem. Soc. 117, 5927 (1995).
40. T. Vaisar, J. Urban and H. Nakanishi, J. Mass Spectrom. 31, 937 (1996).
41. S. S. Wang, J. Am. Chem. Soc. 95, 1328 (1973).
42. R. M. Freidinger, J. S. Hinkle, D. S. Perlow and B. H. Arison, J. Org. Chem. 48, 77 (1983).
43. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Lsikamp M. Lipton, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem. 11, 440 (1990).
44. D. G. Morgan and M. M. Bursey, (a) Org. Mass Spectrom. 29, 354 (1994); (b) J. Mass Spectrom. 30, 595 (1995).
45. D. G. Morgan and M. M. Bursey, (a) Org. Mass Spectrom. 29, 354 (1994); (b) J. Mass Spectrom. 30, 595 (1995).
46. I. A. Kaltashov and C. C. Fenselau, Int. J. Mass Spectrom. Ion Processes 146/147, 339 (1995).
47. T. Vaisar, J. Urban, H. Nakanishi, in Proceedings of the 44th ASMS Conference on Mass Spectrometry and Allied Topics, Portland, OR, 1996, p. 1241.
48. (a) F. W. McLafferty and F. Tureček, Interpretation of Mass Spectra, 4th edn, Chapt. 7. University Science Books, Mill Valley, CA (1993);
49. (b) K. L. Bush, G. L. Glish and S. A. McLuckey, in Mass Spectrometry/Mass Spectrometry: Techniques and Applications of Tandem Mass Spectrometry, Chapt. 3.2. VCH, New York (1988).