ArticleJournal of the American Society for Mass Spectrometry2014
Investigations of the mechanism of the "proline effect" in tandem mass spectrometry experiments: the "pipecolic acid effect".
Article in Journal of the American Society for Mass Spectrometry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 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.
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Who cites it
14 citing papers in PubMed, 36 citations in OpenAlex.
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- Chemo- and regio-selective differential modification of native cysteines on an antibodyChemical science · 2024Article
- Large-scale Bioinformatic Study of Graspimiditides and Structural Characterization of Albusimiditide.ACS chemical biology · 2023Article
- The proline effect and the tryptophan immonium ion assist in de novo sequencing of adipokinetic hormones.Scientific reports · 2023Article
- Targeting proline in (phospho)proteomics.The FEBS journal · 2020Article
- Identification of gene fusion events inNAR genomics and bioinformatics · 2020Article
- Infrared Multiple Photon Dissociation Spectroscopy of Cationized Canavanine: Side-Chain Substitution Influences Gas-Phase Zwitterion FormationInternational journal of mass spectrometry · 2018Article
- N-Protonated Isomers and Coulombic Barriers to Dissociation of Doubly Protonated AlaJournal 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
- Infrared Multiple-Photon Dissociation Action Spectroscopy of the bJournal 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
- Exploitation of the Ornithine Effect Enhances Characterization of Stapled and Cyclic Peptides.Journal of the American Society for Mass Spectrometry · 2016Article
Corrections and comments
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Authors and funding
7 authors at 4 institutions in 1 country.
Funding
Abstract
The fragmentation behavior of a set of model peptides containing proline, its four-membered ring analog azetidine-2-carboxylic acid (Aze), its six-membered ring analog pipecolic acid (Pip), an acyclic secondary amine residue N-methyl-alanine (NMeA), and the D stereoisomers of Pro and Pip has been determined using collision-induced dissociation in ESI-tandem mass spectrometers. Experimental results for AAXAA, AVXLG, AAAXA, AGXGA, and AXPAA peptides are presented, where X represents Pro, Aze, Pip, or NMeA. Aze- and Pro-containing peptides fragment according to the well-established "proline effect" through selective cleavage of the amide bond N-terminal to the Aze/Pro residue to give yn (+) ions. In contrast, Pip- and NMA-fragment through a different mechanism, the "pipecolic acid effect," selectively at the amide bond C-terminal to the Pip/NMA residue to give bn (+) ions. Calculations of the relative basicities of various sites in model peptide molecules containing Aze, Pro, Pip, or NMeA indicate that whereas the "proline effect' can in part be rationalized by the increased basicity of the prolyl-amide site, the "pipecolic acid effect" cannot be justified through the basicity of the residue. Rather, the increased flexibility of the Pip and NMeA residues allow for conformations of the peptide for which transfer of the mobile proton to the amide site C-terminal to the Pip/NMeA becomes energetically favorable. This argument is supported by the differing results obtained for AAPAA versus AA(D-Pro)AA, a result that can best be explained by steric effects. Fragmentation of pentapeptides containing both Pro and Pip indicate that the "pipecolic acid effect" is stronger than the "proline effect."
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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.