ArticleThe journal of physical chemistry. B2010
Gas-phase structure and fragmentation pathways of singly protonated peptides with N-terminal arginine.
Article in The journal of physical chemistry. B, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed.
- Molecular hybridization combining tumor homing and penetrating peptide domains for cellular targeting.Drug delivery and translational research · 2022Article
- Direct Dynamics Simulations of the Thermal Fragmentation of a Protonated Peptide Containing Arginine.ACS omega · 2020Article
- Leaving Group Effects in a Series of Electrosprayed CJournal of the American Society for Mass Spectrometry · 2019Article
- Weak Acid-Base Interactions of Histidine and Cysteine Affect the Charge States, Tertiary Structure, and Zn(II)-Binding of Heptapeptides.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
- Unusual fragmentation of derivatized cysteine-containing peptides.Rapid communications in mass spectrometry : RCM · 2018Article
- 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
- N-Protonated Isomers and Coulombic Barriers to Dissociation of Doubly Protonated AlaJournal 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
- Proton Mobility in b₂ Ion Formation and Fragmentation Reactions of Histidine-Containing Peptides.Journal of the American Society for Mass Spectrometry · 2016Article
- Competing noncovalent host-guest interactions and H/D exchange: reactions of benzyloxycarbonyl-proline glycine dipeptide variants with ND3.Journal of the American Society for Mass Spectrometry · 2015Article
- 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
- Investigation of bn-44 peptide fragments using high resolution mass spectrometry and isotope labeling.Journal of the American Society for Mass Spectrometry · 2014Article
- Loss of internal backbone carbonyls: additional evidence for sequence-scrambling in collision-induced dissociation of y-type ions.Journal of the American Society for Mass Spectrometry · 2014Article
- Mobile proton triggered radical fragmentation of nitroarginine containing peptides.Journal of the American Society for Mass Spectrometry · 2014Article
- Structures of a(n)* ions derived from protonated pentaglycine and pentaalanine: results from IRMPD spectroscopy and DFT calculations.Journal of the American Society for Mass Spectrometry · 2013Article
- Gas Phase Dissociation Behavior of Acyl-Arginine Peptides.International journal of mass spectrometry · 2013Article
- Evidence for sequence scrambling in collision-induced dissociation of y-type fragment ions.Journal of the American Society for Mass Spectrometry · 2013Article
- Non-direct sequence ions in the tandem mass spectrometry of protonated peptide amides--an energy-resolved study.Journal of the American Society for Mass Spectrometry · 2013Article
- Gas-phase fragmentation of oligoproline peptide ions lacking easily mobilizable protons.Journal of the American Society for Mass Spectrometry · 2013Article
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Authors and funding
5 authors.
Funding
Abstract
The gas-phase structures and fragmentation pathways of the singly protonated peptide arginylglycylaspartic acid (RGD) are investigated by means of collision-induced-dissociation (CID) and detailed molecular mechanics and density functional theory (DFT) calculations. It is demonstrated that despite the ionizing proton being strongly sequestered at the guanidine group, protonated RGD can easily be fragmented on charge directed fragmentation pathways. This is due to facile mobilization of the C-terminal or aspartic acid COOH protons thereby generating salt-bridge (SB) stabilized structures. These SB intermediates can directly fragment to generate b(2) ions or facilely rearrange to form anhydrides from which both b(2) and b(2)+H(2)O fragments can be formed. The salt-bridge stabilized and anhydride transition structures (TSs) necessary to form b(2) and b(2)+H(2)O are much lower in energy than their traditional charge solvated counterparts. These mechanisms provide compelling evidence of the role of SB and anhydride structures in protonated peptide fragmentation which complements and supports our recent findings for tryptic systems (Bythell, B. J.; Suhai, S.; Somogyi, A.; Paizs, B. J. Am. Chem. Soc. 2009, 131, 14057-14065.). In addition to these findings we also report on the mechanisms for the formation of the b(1) ion, neutral loss (H(2)O, NH(3), guanidine) fragment ions, and the d(3) ion.
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