ArticleThe journal of physical chemistry. A2012
Structural influences on preferential oxazolone versus diketopiperazine b(2+) ion formation for histidine analogue-containing peptides.
Article in The journal of physical chemistry. A, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 37 citations in OpenAlex.
- Competition between Charge- and Radical-Driven Dissociations in the Molecular Radical Cations of Tripeptides.ACS physical chemistry Au · 2026Article
- A spectroscopic test suggests that fragment ion structure annotations in MS/MS libraries are frequently incorrect.Communications chemistry · 2024Article
- Water Loss from Protonated XxxSer and XxxThr Dipeptides Gives Oxazoline-Not Oxazolone-Product Ions.Journal of the American Society for Mass Spectrometry · 2020Article
- 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
- Participation of C-H Protons in the Dissociation of a Proton Deficient Dipeptide.Journal of the American Society for Mass Spectrometry · 2017Article
- Proton Mobility in b₂ Ion Formation and Fragmentation Reactions of Histidine-Containing Peptides.Journal of the American Society for Mass Spectrometry · 2016Article
- Formation of a(1) ions directly from oxazolone b(2) ions: an energy-resolved and computational study.Journal of the American Society for Mass Spectrometry · 2015Article
- Article
- Evidence for sequence scrambling and divergent H/D exchange reactions of doubly-charged isobaric b-type fragment ions.Journal of the American Society for Mass Spectrometry · 2014Article
- Spectroscopic identification of cyclic imide b2-ions from peptides containing Gln and Asn residues.Journal of the American Society for Mass Spectrometry · 2013Article
- Influence of N-terminal residue composition on the structure of proline-containing b2+ ions.The journal of physical chemistry. A · 2013Article
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
Studies of peptide fragment ion structures are important to aid in the accurate kinetic modeling and prediction of peptide fragmentation pathways for a given sequence. Peptide b(2)(+) ion structures have been of recent interest. While previously studied b(2)(+) ions that contain only aliphatic or simple aromatic residues are oxazolone structures, the HA b(2)(+) ion consists of both oxazolone and diketopiperazine structures. The structures of a series of histidine-analogue-containing Xxx-Ala b(2)(+) ions were studied by using action infrared multiphoton dissociation (IRMPD) spectroscopy, fragment ion hydrogen-deuterium exchange (HDX), and density functional theory (DFT) calculations to systematically probe the influence of different side chain structural elements on the resulting b(2)(+) ion structures formed. The b(2)(+) ions studied include His-Ala (HA), methylated histidine analogues, including π-methyl-HA and τ-methyl-HA, pyridylalanine (pa) analogues, including 2-(pa)A, 3-(pa)A, and 4-(pa)A, and linear analogues, including diaminobutanoic acid-Ala (DabA) and Lys-Ala (KA). The location and accessibility of the histidine π-nitrogen, or an amino nitrogen on an aliphatic side chain, were seen to be essential for diketopiperazine formation in addition to the more typical oxazolone structure formation, while blocking or removal of the τ-nitrogen did not change the b(2)(+) ion structures formed. Linear histidine analogues, DabA and KA, formed only diketopiperazine structures, suggesting that a steric interaction in the HisAla case may interfere with the complete trans-cis isomerization of the first amide bond that is necessary for diketopiperazine formation.
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