2008
DOI: 10.1016/j.jasms.2008.09.007
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Canα- andβ-alanine containing peptides Be distinguished based on the CID spectra of their protonated ions?

Abstract: The fragmentation reactions of isomeric dipeptides containing ␣-and ␤-alanine residues (␣Ala-␣Ala, ␣Ala-␤Ala, ␤Ala-␣Ala, and ␤Ala-␤Ala) were studied using a combination of low-energy and energy resolved collision induced dissociation (CID). Each dipeptide gave a series of different fragment ions, allowing for differentiation. For example, peptides containing an N-terminal ␤-Ala residue yield a diagnostic imine loss, while lactam ions at m/z 72 are unique to peptides containing ␤-Ala residues. In addition, MS 3… Show more

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Cited by 6 publications
(8 citation statements)
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“…1(B), the introduction of the methyl ester also promotes the fragmentation of β 2 ‐phenylalanine via NH 3 loss ( m / z 163). In addition, it introduces a variety of minor abundance ions not observed before, including a water adduct at m / z 166 and NHCH 2 loss (to yield the ion at m / z 151), probably occurring via a retro‐Mannich mechanism discussed previously 19, 20, 25. Collisional activation of protonated β 2 ‐phenylalanine‐NHCH 3 alters the preferred fragmentation pathways dramatically, with the dominant channel now being loss of NH 3 at m / z 162, with only a minor amount of NHCH 2 loss ( m / z 150) being observed.…”
Section: Resultsmentioning
confidence: 89%
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“…1(B), the introduction of the methyl ester also promotes the fragmentation of β 2 ‐phenylalanine via NH 3 loss ( m / z 163). In addition, it introduces a variety of minor abundance ions not observed before, including a water adduct at m / z 166 and NHCH 2 loss (to yield the ion at m / z 151), probably occurring via a retro‐Mannich mechanism discussed previously 19, 20, 25. Collisional activation of protonated β 2 ‐phenylalanine‐NHCH 3 alters the preferred fragmentation pathways dramatically, with the dominant channel now being loss of NH 3 at m / z 162, with only a minor amount of NHCH 2 loss ( m / z 150) being observed.…”
Section: Resultsmentioning
confidence: 89%
“…Water loss appears to be a diagnostic reaction channel that allows differentiation between the three isomers. It is worth noting that water loss has also been observed for β‐alanine,18, 19 which contrasts with the virtual absence of water loss for α‐alanine 35. Possible mechanisms for these small molecule losses are shown in Scheme .…”
Section: Resultsmentioning
confidence: 97%
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“…Its attachment to the side chain of a lysine may prevent cleavage with trypsin, a frequent strategy used to sequence proteins. In addition, β‐alanine is an isomer of α‐alanine, and therefore requires specific attention for detection by mass spectrometry .…”
Section: Discussionmentioning
confidence: 99%
“…This in turn increased the interest in the fragmentation pathways of protonated peptides and the mechanisms of product ion formation which spurred several studies on protonated a-amino acids, [23][24][25][26][27][28][29][30] while studies on b-amino acids or peptides that contain them remain very sparse. 31,32 Relatively simple CID mass spectra are generated due to the fragmentation of protonated aliphatic a-amino acids which mainly show their respective iminium ions produced via the concomitant loss of H 2 O and CO. Hydroxylic and acidic a-amino acids lose H 2 O through the OH and COOH groups in their side chains in addition to the concomitant loss of H 2 O and CO. Basic a-amino acids such as arginine and lysine have a nitrogen on the side chain as the favoured site of protonation 30 thus one of the major fragmentation pathways in these amino acids involves the loss of NH 3 and, in the case of protonated arginine, guanidine.…”
Section: Introductionmentioning
confidence: 99%