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- W2107212644 abstract "The presence and position of a single β-alanine (βA), γ-aminobutyric acid (γABu) or ε-aminocaproic acid (Cap) residue has been shown to have a significant influence on the formation of bn+ and yn+ product ions from a series of model, protonated peptides. In this study, we examined the effect of the same residues on the formation of analogous [b3 − 1 + cat]+ products from metal(Li+, Na+ and Ag+)-cationized peptides. The larger amino acids suppress formation of b3+ from protonated peptides with general sequence AAXG (where X = β-alanine, γ-aminobutyric acid or ε-aminocaproic acid), presumably because of the prohibitive effect of larger cyclic intermediates in the ‘oxazolone’ pathway. However, abundant [b3 − 1 + cat]+ products are generated from metal-cationized versions of AAXG. Using a group of deuterium-labeled and exchanged peptides, we found that formation of [b3 − 1 + cat]+ involves transfer of either amide or α-carbon position H atoms, and the tendency to transfer the atom from the α-carbon position increases with the size of the amino acid in position X. To account for the transfer of the H atom, a mechanism involving formation of a ketene product as [b3 − 1 + cat]+ is proposed. Copyright © 2008 John Wiley & Sons, Ltd." @default.
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- W2107212644 date "2008-11-01" @default.
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- W2107212644 title "Formation of [b3− 1 + cat]+ions from metal-cationized tetrapeptides containing β-alanine, γ-aminobutyric acid or ε-aminocaproic acid residues" @default.
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- W2107212644 doi "https://doi.org/10.1002/jms.1418" @default.
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