ArticleJournal of mass spectrometry : JMS2013
The ornithine effect in peptide cation dissociation.
Article in Journal of mass spectrometry : JMS, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
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.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
22 citing papers in PubMed.
- Understanding the selectivityFrontiers in bioinformatics · 2025Article
- Imaging Mass Spectrometry of Sulfatide Isomers from Rat Brain Tissue Using Gas-Phase Charge Inversion Ion/Ion Reactions.Journal of the American Society for Mass Spectrometry · 2025Article
- Structural Elucidation and Relative Quantification of Fatty Acid Double Bond Positional Isomers in Biological Tissues Enabled by Gas-Phase Charge Inversion Ion/Ion Reactions.Analysis & sensing · 2024Article
- Relative Quantification of Lipid Isomers in Imaging Mass Spectrometry Using Gas-Phase Charge Inversion Ion/Ion Reactions and Infrared Multiphoton Dissociation.Analytical chemistry · 2023Article
- Early Selection of the Amino Acid Alphabet Was Adaptively Shaped by Biophysical Constraints of Foldability.Journal of the American Chemical Society · 2023Article
- 2-Pyridine Carboxaldehyde for Semi-Automated Soft Spot Identification in Cyclic Peptides.International journal of molecular sciences · 2022Article
- Quantification of the Effect of Citrulline and Homocitrulline Residues on the Collision-Induced Fragmentation of Peptides.Journal of the American Society for Mass Spectrometry · 2020Article
- Gas-Phase Sequencing of Cyclotides: Introduction of Selective Ring Opening at Dehydroalanine via Ion/Ion Reaction.Analytical chemistry · 2019Article
- Gold(I) Cationization Promotes Ring Opening in Lysine-Containing Cyclic Peptides.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
- Gas-Phase Ion/Ion Chemistry as a Probe for the Presence of Carboxylate Groups in Polypeptide Cations.Journal of the American Society for Mass Spectrometry · 2019Article
- Maximizing Selective Cleavages at Aspartic Acid and Proline Residues for the Identification of Intact Proteins.Journal of the American Society for Mass Spectrometry · 2019Article
- Isolation of a jadomycin incorporating L-ornithine, analysis of antimicrobial activity and jadomycin reactive oxygen species (ROS) generation in MDA-MB-231 breast cancer cells.The Journal of antibiotics · 2018Article
- The Generation of Dehydroalanine Residues in Protonated Polypeptides: Ion/Ion Reactions for Introducing Selective Cleavages.Journal of the American Society for Mass Spectrometry · 2017Article
- An Electrospray Ionization Mass Spectrometry Study on the "In Vacuo" Hetero-Oligomers Formed by the Antimicrobial Peptides, Surfactin and Gramicidin S.Journal of the American Society for Mass Spectrometry · 2017Article
- The dehydroalanine effect in the fragmentation of ions derived from polypeptides.Journal of mass spectrometry : JMS · 2016Article
- Exploitation of the Ornithine Effect Enhances Characterization of Stapled and Cyclic Peptides.Journal of the American Society for Mass Spectrometry · 2016Article
- C-terminal peptide extension via gas-phase ion/ion reactions.International journal of mass spectrometry · 2015Article
- Gas-Phase Amidation of Carboxylic Acids with Woodward's Reagent K Ions.Journal of the American Society for Mass Spectrometry · 2015Article
- Comparison of Ultraviolet Photodissociation and Collision Induced Dissociation of Adrenocorticotropic Hormone Peptides.Journal of the American Society for Mass Spectrometry · 2015Article
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
Facile cleavage C-terminal to ornithine residues in gas phase peptides has been observed and termed the ornithine effect. Peptides containing internal or C-terminal ornithine residues, which are formed from deguanidination of arginine in solution, were fragmented to produce either a y-ion or water loss, respectively, and the complementary b-ion. The fragmentation patterns of several peptides containing arginine were compared to those of the ornithine analogues. Conversion of arginine to ornithine results in a decrease of the gas phase proton affinity of the residue, thereby increasing the mobility of the ionizing proton. This alteration allows the nucleophilic amine to facilitate a neighboring group reaction to induce a cleavage of the adjacent amide bond. The selective cleavage at the ornithine residue is proposed to result from the highly favorable generation of a six-membered lactam ring. The ornithine effect was compared with the well-known proline and aspartic acid effects in peptide fragmentation using angiotensin II, DRVYIHPF and the ornithine analogue, DOVYIHPF. Under conditions favorable to either the aspartic acid (i.e. singly protonated peptide) or proline effect (i.e. doubly protonated peptide), the ornithine effect was consistently observed to be the more favorable fragmentation pathway. The highly selective nature of the ornithine effect opens up the possibility for conversion of arginine to ornithine residues to induce selective cleavages in polypeptide ions. Such an approach may complement strategies that seek to generate non-selective cleavages of the related peptides.
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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.