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Record W2081489224 · doi:10.1016/j.jasms.2009.07.002

Fragmentation of doubly-protonated Pro-His-Xaa tripeptides: Formation of <i>b</i><sub><i>2</i></sub><sup><i>2</i>+</sup> ions

2009· article· he· W2081489224 on OpenAlexaff
Michaela Knapp‐Mohammady, Alex B. Young, Béla Paizs, Alex G. Harrison

Bibliographic record

VenueJournal of the American Society for Mass Spectrometry · 2009
Typearticle
Languagehe
FieldChemistry
TopicMass Spectrometry Techniques and Applications
Canadian institutionsUniversity of Toronto
Fundersnot available
KeywordsChemistryProtonationOxazoloneTripeptideFragmentation (computing)Collision-induced dissociationIonCrystallographyStereochemistryIminiumDissociation (chemistry)NucleophileComputational chemistryMass spectrometryTandem mass spectrometryPeptideOrganic chemistry

Abstract

fetched live from OpenAlex

When ionized by electrospray from acidic solutions, the tripeptides Pro-His-Xaa (Xaa = Gly, Ala, Leu) form abundant doubly-protonated ions, [M + 2H]2+. Collision-induced dissociation (CID) of these doubly-protonated species results, in part, in formation of b(2)(2+) ions, which fragment further by loss of CO to form a(2)(2+) ions; the latter fragment by loss of CO to form the Pro and His iminium [immonium is commonly used in peptide MS work] ions. Although larger doubly-charged b ions are known, this represents the first detailed study of b(2)(2+) ions in CID of small doubly protonated peptides. The most abundant CID products of the studied doubly-protonated peptides arise mainly in charge separation involving two primary fragmentation channels, formation of the b2/y1 pair and formation of the a1/y2 pair. Combined molecular dynamics and density functional theory calculations are used to gain insight into the structures and fragmentation pathways of doubly-protonated Pro-His-Gly including the energetics of potential protonation sites, backbone cleavages, post-cleavage charge-separation reactions and the isomeric structures of b(2)(2+) ions. Three possible structures are considered for the b(2)(2+) ions: the oxazolone, diketopiperazine, and fused ring isomers. The last is formed by cleavage of the His-Gly amide bond on a pathway that is initiated by nucleophilic attack of one of the His side-chain imidazole nitrogens. Our calculations indicate the b(2)(2+) ion population is dominated by the oxazolone and/or fused ring isomers.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesMeta-epidemiology (narrow)
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.020
Threshold uncertainty score1.000

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0010.001
Meta-epidemiology (broad)0.0020.003
Bibliometrics0.0000.004
Science and technology studies0.0000.001
Scholarly communication0.0000.001
Open science0.0020.000
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0000.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.013
GPT teacher head0.272
Teacher spread0.259 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations27
Published2009
Admission routes1
Has abstractyes

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