Sequencing of β-peptides by mass spectrometry

Chimia

Volumn 53, Issue 12, 1999, Pages 621-626

  Schreiber, Jürg V ^a   Quadroni, Manfrede ^a   Seebach, Dieter ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033478785     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Part of the projected Ph. D. thesis of J.V.S, ETH Zurich.
2. P. Gaff, Novartis Pharma AG, BMP, Basel; hitherto unpublished results.
3. P. Edman, Nature 1956, 777, 667.
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5. J. Podlech, D. Seebach, Angew. Chem. 1995, 107, 507; ibid. Int. Ed. Engl. 1995, 34, 471; J. Podlech, D. Seebach, Liebigs Ann. Chem. 1995, 1217.
6. J. Podlech, D. Seebach, Angew. Chem. 1995, 107, 507; ibid. Int. Ed. Engl. 1995, 34, 471; J. Podlech, D. Seebach, Liebigs Ann. Chem. 1995, 1217.
7. Reviews: D. Seebach, J.L. Matthews, Chem. Commun. 1997, 2015; S.H. Gellman, Acc. Chem. Res. 1998, 31, 173; K. Gademann, T. Hintermann, J.V. Schreiber, Curr. Med. Chem. 1999, 6, 905; W.F. DeGrado, J.P. Schneider, Y. Hamuro, J. Peptide Res. 1999, 54, 206.
8. Reviews: D. Seebach, J.L. Matthews, Chem. Commun. 1997, 2015; S.H. Gellman, Acc. Chem. Res. 1998, 31, 173; K. Gademann, T. Hintermann, J.V. Schreiber, Curr. Med. Chem. 1999, 6, 905; W.F. DeGrado, J.P. Schneider, Y. Hamuro, J. Peptide Res. 1999, 54, 206.
9. Reviews: D. Seebach, J.L. Matthews, Chem. Commun. 1997, 2015; S.H. Gellman, Acc. Chem. Res. 1998, 31, 173; K. Gademann, T. Hintermann, J.V. Schreiber, Curr. Med. Chem. 1999, 6, 905; W.F. DeGrado, J.P. Schneider, Y. Hamuro, J. Peptide Res. 1999, 54, 206.
10. Reviews: D. Seebach, J.L. Matthews, Chem. Commun. 1997, 2015; S.H. Gellman, Acc. Chem. Res. 1998, 31, 173; K. Gademann, T. Hintermann, J.V. Schreiber, Curr. Med. Chem. 1999, 6, 905; W.F. DeGrado, J.P. Schneider, Y. Hamuro, J. Peptide Res. 1999, 54, 206.
11. W. Paul, Angew. Chem. 1990, 102, 780; ibid. Int. Ed. Engl. 1990, 29, 739; P. James, Quarterly Review of Biophysics 1997, 30, 279.
12. W. Paul, Angew. Chem. 1990, 102, 780; ibid. Int. Ed. Engl. 1990, 29, 739; P. James, Quarterly Review of Biophysics 1997, 30, 279.
13. W. Paul, Angew. Chem. 1990, 102, 780; ibid. Int. Ed. Engl. 1990, 29, 739; P. James, Quarterly Review of Biophysics 1997, 30, 279.
14. J.V.S., hitherto unpublished results, ETH Zürich, 1999.
15. G. Guichard, S. Abele, D. Seebach, Helv. Chim. Acta 1998, 52, 187.
16. S. Abele, G. Guichard, D. Seebach, Helv. Chim. Acta 1998, 81, 2141.
17. D. Seebach, J. V. Schreiber, S. Abele, X. Daura, Helv. Chim. Acta 2000, in preparation.
18. D. Seebach, M. Overhand, F.N.M. Kühnle, B. Martinoni, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1996, 79, 913.
19. D. Seebach, S. Abele, K. Gademann, G. Guichard, T. Hintermann, B. Jaun, J.L. Matthews, J.V. Schreiber, L. Oberer, U. Hommel, H. Widmer, Helv. Chim. Acta 1998, 81, 932.
20. T. Hintermann, D. Seebach, Synlett 1997, 437.
21. The interpreted spectra of the β-peptides 3-7 and of their derivatives are available as supplementary material and can be requested free of charge from the editor of CHIMIA.
22. P. Roepstorff, J. Fohlman, Biomed. Environ. Mass Spectrom. 1984, 11, 601.
23. K. Biemann, Biomed. Environ. Mass Spec. 1988,16, 99.
24. J. Taylor, K. Walsh, R. Johnson, Rapid, Commun. Mass Spectrom. 1996, 10, 679.
25. -5 Torr, without decomposition (D. Seebach, P.E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz, H. Widmer, Helv. Chim. Acta 1996, 79, 2043).
26. -5 Torr, without decomposition (D. Seebach, P.E. Ciceri, M. Overhand, B. Jaun, D. Rigo, L. Oberer, U. Hommel, R. Amstutz, H. Widmer, Helv. Chim. Acta 1996, 79, 2043).
27. 2-CO⊕ ion to lose CO from a β-peptide than for an R-NH-CHR'-CO⊕ ion from an α-peptide (retro-Koch reaction).
28. See, e.g., R.E. Marti, K.H. Bleicher, K.W. Bair, Tetrahedron Letters 1997, 38, 6145.