ArticleJournal of the American Society for Mass Spectrometry2016
Proton Mobility in b₂ Ion Formation and Fragmentation Reactions of Histidine-Containing Peptides.
Article in Journal of the American Society for Mass Spectrometry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 21 citations in OpenAlex.
- Characteristic Fragmentation Behavior of Linear and CyclicMolecules (Basel, Switzerland) · 2025Article
- Influence of N Terminus Amino Acid on Peptide Cleavage in Solution through Diketopiperazine Formation.Journal of the American Society for Mass Spectrometry · 2022Article
- Mass spectral and theoretical investigations of the transient proton-bound dimers on the cleavage processes of the peptide GHK and its analogues.RSC advances · 2021Article
- Leaving Group Effects in a Series of Electrosprayed CJournal of the American Society for Mass Spectrometry · 2019Article
- Weak Acid-Base Interactions of Histidine and Cysteine Affect the Charge States, Tertiary Structure, and Zn(II)-Binding of Heptapeptides.Journal of the American Society for Mass Spectrometry · 2019Article
- Spectroscopic Evidence for Lactam Formation in Terminal Ornithine bJournal of the American Society for Mass Spectrometry · 2019Article
- Comment on: "Quantum Chemical Mass Spectrometry: Verification and Extension of the Mobile Proton Model for Histidine" by Julie Cautereels and Frank Blockhuys, J. Am. Soc. Mass Spectrom. 28, 1227-1235 (2017).Journal of the American Society for Mass Spectrometry · 2017Article
- Cationized Carbohydrate Gas-Phase Fragmentation Chemistry.Journal of the American Society for Mass Spectrometry · 2017Article
- Stereochemical Sequence Ion Selectivity: Proline versus Pipecolic-acid-containing Protonated Peptides.Journal of the American Society for Mass Spectrometry · 2017Article
- Difference of Electron Capture and Transfer Dissociation Mass Spectrometry on Ni(2+)-, Cu(2+)-, and Zn(2+)-Polyhistidine Complexes in the Absence of Remote Protons.Journal of the American Society for Mass Spectrometry · 2016Article
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Authors and funding
4 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
A detailed energy-resolved study of the fragmentation reactions of protonated histidine-containing peptides and their b2 ions has been undertaken. Density functional theory calculations were utilized to predict how the fragmentation reactions occur so that we might discern why the mass spectra demonstrated particular energy dependencies. We compare our results to the current literature and to synthetic b2 ion standards. We show that the position of the His residue does affect the identity of the subsequent b2 ion (diketopiperazine versus oxazolone versus lactam) and that energy-resolved CID can distinguish these isomeric products based on their fragmentation energetics. The histidine side chain facilitates every major transformation except trans-cis isomerization of the first amide bond, a necessary prerequisite to diketopiperazine b2 ion formation. Despite this lack of catalyzation, trans-cis isomerization is predicted to be facile. Concomitantly, the subsequent amide bond cleavage reaction is rate-limiting.
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