ArticleJournal of the American Society for Mass Spectrometry2005
Computational investigation and hydrogen/deuterium exchange of the fixed charge derivative tris(2,4,6-trimethoxyphenyl) phosphonium: implications for the aspartic acid cleavage mechanism.
Article in Journal of the American Society for Mass Spectrometry, 2005. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed.
- Article
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- Combinatorial Labeling Method for Improving Peptide Fragmentation in Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2017Article
- Ion Mobility Spectrometry-Hydrogen Deuterium Exchange Mass Spectrometry of Anions: Part 3. Estimating Surface Area Exposure by Deuterium Uptake.Journal of the American Society for Mass Spectrometry · 2016Article
- Charge site assignment in native proteins by ultraviolet photodissociation (UVPD) mass spectrometry.The Analyst · 2016Article
- A density functional theory study on peptide bond cleavage at aspartic residues: direct vs cyclic intermediate hydrolysis.Journal of molecular modeling · 2013Article
- Theoretical study on isomerization and peptide bond cleavage at aspartic residue.Journal of molecular modeling · 2013Article
- The influence glutamic acid in protonated bInternational journal of mass spectrometry · 2012Article
- Structural influences on preferential oxazolone versus diketopiperazine b(2+) ion formation for histidine analogue-containing peptides.The journal of physical chemistry. A · 2012Article
- Tandem mass spectrometric characterization of thiol peptides modified by the chemoselective cationic sulfhydryl reagent (4-iodobutyl)triphenylphosphonium--effects of a cationic thiol derivatization on peptide fragmentation.Journal of the American Society for Mass Spectrometry · 2011Article
- Influence of amino acid side chains on apparent selective opening of cyclic b5 ions.Journal of the American Society for Mass Spectrometry · 2010Article
- Gas-Phase Hydrogen/Deuterium Exchange of Dinucleotides and 5'-Monophosphate Dinucleotides in a Quadrupole Ion Trap.International journal of mass spectrometry · 2009Article
- Fragmentation mechanisms of oxidized peptides elucidated by SID, RRKM modeling, and molecular dynamics.Journal of the American Society for Mass Spectrometry · 2009Article
- Probing peptide fragment ion structures by combining sustained off-resonance collision-induced dissociation and gas-phase H/D exchange (SORI-HDX) in Fourier transform ion-cyclotron resonance (FT-ICR) instruments.Journal of the American Society for Mass Spectrometry · 2008Article
- Isomeric differentiation of green tea catechins using gas-phase hydrogen/deuterium exchange reactions.Journal of the American Society for Mass Spectrometry · 2007Article
- Conformationally driven gas-phase H/D exchange of dinucleotide negative ions.Journal of the American Society for Mass Spectrometry · 2007Article
- Gas-phase hydrogen/deuterium exchange of 5'- and 3'-mononucleotides in a quadrupole ion trap: exploring the role of conformation and system energy.Journal of the American Society for Mass Spectrometry · 2007Article
- Aspartic acid side chain effect-experimental and theoretical insight.Journal of the American Society for Mass Spectrometry · 2007Article
- Fragmentation of doubly-protonated peptide ion populations labeled by H/D exchange with CD(3)OD.International journal of mass spectrometry · 2006Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Aspartic acid (Asp)-containing peptides with the fixed charge derivative tris(2,4,6trimethoxyphenyl) phosphonium (tTMP-P+) were explored computationally and experimentally by hydrogen/deuterium (H/D) exchange and by fragmentation studies to probe the phenomenon of selective cleavage C-terminal to Asp in the absence of a "mobile" proton. Ab initio modeling of the tTMP-P+ electrostatic potential shows that the positive charge is distributed on the phosphonium group and therefore is not initiating or directing fragmentation as would a "mobile" proton. Geometry optimizations and vibrational analyses of different Asp conformations show that the Asp structure with a hydrogen bond between the side-chain hydroxy and backbone carbonyl lies 2.8 kcal/mol above the lowest energy conformer. In reactions with D2O, the phosphonium-derived doubly charged peptide (H+)P+LDIFSDF rapidly exchanges all 12 of its exchangeable hydrogens for deuterium and also displays a nonexchanging population. With no added proton, P+LDIFSDF exchanges a maximum of 4 of 11 exchangeable hydrogens for deuterium. No exchange is observed when all acidic groups are converted to the corresponding methyl esters. Together, these H/D exchange results indicate that the acidic hydrogens are "mobile locally" because they are able to participate in exchange even in the absence of an added proton. Fragmentation of two distinct (H+)P+LDIFSDF ion populations shows that the nonexchanging population displays selective cleavage, whereas the exchanging population fragments more evenly across the peptide backbone. This result indicates that H/D exchange can sometimes distinguish between and provide a means of separation of different protonation motifs and that these protonation motifs can have an effect on the fragmentation.
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