ArticleThe Analyst2014
IR action spectroscopy shows competitive oxazolone and diketopiperazine formation in peptides depends on peptide length and identity of terminal residue in the departing fragment.
Article in The Analyst, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
8 citing papers in PubMed, 17 citations in OpenAlex.
- Competition between Charge- and Radical-Driven Dissociations in the Molecular Radical Cations of Tripeptides.ACS physical chemistry Au · 2026Article
- Protonation-Induced Chemical Transformations in Mass Spectrometry: Implications for Detecting Complex Organics on Icy Moons.ACS earth & space chemistry · 2026Article
- Infrared multiple photon dissociation (IRMPD) spectroscopy and its potential for the clinical laboratory.Journal of mass spectrometry and advances in the clinical lab · 2022Article
- 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
- Infrared Multiple-Photon Dissociation Action Spectroscopy of the bJournal 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
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
Abstract
The interplay between the entropically and enthalpically favored products of peptide fragmentation is probed using a combined experimental and theoretical approach. These b2 ion products can take either an oxazolone or diketopiperazine structure. Cleavage after the second amide bond is often a favorable process because the products are small ring structures that are particularly stable. These structures are structurally characterized by action IRMPD spectroscopy and semi-quantified using gas-phase hydrogen-deuterium exchange. The formation of the oxazolone and diketopiperazine has been thought to be largely governed by the identity of the first two residues at the N-terminus of the peptide. We show here that the length of the precursor peptide and identity of the third residue play a significant role in the formation of the diketopiperazine structure in peptides containing an N-terminal asparagine residue. This is additionally the first instance showing an N-terminal residue with an amide side chain can promote formation of the diketopiperazine b2 ion structure.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.