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Open Access Sequencing of β-Peptides by Mass Spectrometry

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Seven β-peptides containing up to 18 β2-, β 3- and β2,3-amino acids have been subjected to ESI-tandem mass spectrometry (low-energy fragmentation, positive ions). From the fragment ions formed from the free β-peptides, as well as from the corresponding methyl esters (+14 U) and N-acetyl derivatives (+42 U), the known sequences of β-amino acids could be confirmed unambiguously with the program Sherpa. Thus, the commonly used MS-sequencing procedure for α-peptides can be adopted for β-peptides without modification. However, there are pronounced differences in the fragmentation patterns of the two types of peptides: the β-peptides disclose their relationship to Mannich bases in the mass-spectrometric experiment by the elimination of ammonia from the N-terminus (→ RCH=CH-CO-NH-R') and the occurence of retro-Mannich cleavage (cf. formation of HN=CHR + CH3CO-NH-R' from β-amino-acid residues).
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Document Type: Miscellaneous

Publication date: December 1, 1999

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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