Side-chain involvement in the fragmentation reactions of the protonated methyl esters of histidine and its peptides†

No abstract is available for this paper.

• Publication year

  2001

• Venue

  International Journal of Mass Spectrometry

• Publication date

  2001-09-25

• Fields of study

  Chemistry

• Identifiers
  DOI 10.1016/S1387-3806(01)00443-2
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar

• No claims are published for this paper.

• No concepts are published for this paper.

• Effect of adjacent histidine and cysteine residues on the spontaneous degradation of asparaginyl- and aspartyl-containing peptides.

  2009cited by this paper
• Proteome Research: Two-Dimensional Gel Electrophoresis and Identification Methods

  2000cited by this paper
• Ab initio insights into amide bond cleavage reactions of formamide with substituted methyl cations XCH2+ (X = OH, F, and Cl)

  2000cited by this paper
• Fragmentation mechanisms of α-amino acids protonated under electrospray ionization: a collisional activation and ab initio theoretical study

  2000cited by this paper
• Proteomics, peptide sequencing and the fragmentation mechanisms of small organic ions

  2000cited by this paper
• Leaving group and gas phase neighboring group effects in the side chain losses from protonated serine and its derivatives

  2000cited by this paper
• The search for stable gas phase b(1) ions derived from aliphatic amino acids: a combined experimental and ab initio study.

  2000cited by this paper
• Dissociation of the peptide bond in protonated peptides.

  2000cited by this paper
• The role of nucleophile--electrophile interactions in the unimolecular and bimolecular gas-phase ion chemistry of peptides and related systems.

  2000cited by this paper
• Formation of a2+ ions of protonated peptides. An ab initio study.

  2000cited by this paper
• Structure and fragmentation of b2 ions in peptide mass spectra

  2000cited by this paper
• Five-membered ring formation in unimolecular reactions of peptides: a key structural element controlling low-energy collision-induced dissociation of peptides.

  2000cited by this paper
• Mobile and localized protons: a framework for understanding peptide dissociation.

  2000cited by this paper
• Neighboring Group versus Cis-Elimination Mechanisms for Side Chain Loss from Protonated Methionine, Methionine Sulfoxide and Their Peptides

  1999cited by this paper
• Structural basis for amide hydrolysis catalyzed by the 43C9 antibody.

  1999cited by this paper
• Probing the fragmentation reactions of protonated glycine oligomers via multistage mass spectrometry and gas phase ion molecule hydrogen/deuterium exchange

  1999cited by this paper
• Electron distribution in cationic fragments generated mass spectrometrically from peptides

  1999cited by this paper
• Characterization of an ambident electrophile: the gas phase reactivity of the methoxymethyl cation

  1998cited by this paper
• Origin of product ions in the MS/MS spectra of peptides in a quadrupole ion trap

  1998cited by this paper
• Role of the sulfhydryl group on the gas phase fragmentation reactions of protonated cysteine and cysteine containing peptides

  1998cited by this paper
• A mass spectrometric and ab initio study of the pathways for dehydration of simple glycine and cysteine-containing peptide [M+H]+ ions

  1998cited by this paper
• Cooperative Nucleophilic and General-Acid Catalysis by the HisH+−His Pair and Arginine Transition State Binding in Catalysis of Ester Hydrolysis Reactions by Designed Helix−Loop−Helix Motifs

  1998cited by this paper
• Distinction of N-substituted histidines by electrospray ionization mass spectrometry.

  1998cited by this paper
• Gas‐phase fragmentation of protonated mono‐N‐methylated peptides. Analogy with solution‐phase acid‐catalyzed hydrolysis

  1998cited by this paper
• Low-Energy Collision Induced Dissociation of Protonated Peptides. Importance of an Oxazolone Formation for a Peptide Bond Cleavage

  1998cited by this paper
• Amide bond dissociation in protonated peptides. Structures of the N-terminal ionic and neutral fragments

  1997cited by this paper
• Pathways to Immonium Ions in the Fragmentation of Protonated Peptides

  1997cited by this paper
• THE METHOXYMETHYL CATION CLEAVES PEPTIDE BONDS IN THE GAS PHASE

  1997cited by this paper
• Proton mobility in protonated amino acids and peptides

  1997cited by this paper
• Influence of Peptide Composition, Gas-Phase Basicity, and Chemical Modification on Fragmentation Efficiency: Evidence for the Mobile Proton Model

  1996cited by this paper
• Gas-phase basicities of histidine and lysine and their selected di- and tripeptides

  1996cited by this paper
• The structure and fragmentation of Bn (n≥3) ions in peptide spectra

  1996cited by this paper
• Histidyl-glycyl containing peptides. Characterization complexation properties of H(L-His-Gly)2-R with hydrogen and alkali metal ions in the gas phase.

  1996cited by this paper
• Harmonic Vibrational Frequencies: An Evaluation of Hartree−Fock, Møller−Plesset, Quadratic Configuration Interaction, Density Functional Theory, and Semiempirical Scale Factors

  1996cited by this paper
• Why Are B ions stable species in peptide spectra?

  1995cited by this paper
• UNIMOLECULAR CHEMISTRY OF PROTONATED FORMAMIDE. MASS SPECTROMETRY AND AB INITIO QUANTUM CHEMICAL CALCULATIONS

  1994cited by this paper
• Amino Acid Sequencing of Proteins

  1994cited by this paper
• The effect of protonation site on bond strengths in simple peptides: Application of Ab initio and modified neglect of differential overlap bond orders and modified neglect of differential overlap energy partitioning

  1994cited by this paper
• Structural Determinants of Gas Phase Basicities of Peptides

  1993cited by this paper
• Proposal for a common nomenclature for sequence ions in mass spectra of peptides.

  1984cited by this paper
• Self‐consistent molecular orbital methods. XXIII. A polarization‐type basis set for second‐row elements

  1982cited by this paper
• Self‐consistent molecular orbital methods. XV. Extended Gaussian‐type basis sets for lithium, beryllium, and boron

  1975cited by this paper
• The influence of polarization functions on molecular orbital hydrogenation energies

  1973cited by this paper
• A Novel Peptide Cleavage Reaction

  1963cited by this paper

• Gas Phase Fragmentation Behavior of Proline in Macrocyclic b7 Ions

  2023cites this paper
• Mass spectral and theoretical investigations of the transient proton-bound dimers on the cleavage processes of the peptide GHK and its analogues

  2021cites this paper
• QUANTUM CHEMICAL MASS SPECTROMETRY: AB INITIO STUDY OF b2 -ION FORMATION MECHANISMS FOR THE SINGLY PROTONATED GLN-HIS-SER TRIPEPTIDE.

  2020cites this paper
• Water Loss from Protonated XxxSer and XxxThr Dipeptides Gives Oxazoline—Not Oxazolone—Product Ions

  2020cites this paper
• Gas-Phase Fragmentation Chemistry of Small Ions

  2019cites this paper
• Characterization of acetylated histidine b1-ion structure: A competition between oxazolone and side chain imidazole moiety

  2018cites this paper
• 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)

  2017cites this paper
• Dehydration reactions of protonated dipeptides containing asparagine or glutamine investigated by infrared ion spectroscopy

  2017cites this paper
• Participation of C-H Protons in the Dissociation of a Proton Deficient Dipeptide

  2017cites this paper
• Proton Mobility in b2 Ion Formation and Fragmentation Reactions of Histidine-Containing Peptides

  2016cites this paper
• Stereochemical Sequence Ion Selectivity: Proline versus Pipecolic-acid-containing Protonated Peptides

  2016cites this paper
• Gas-Phase Folding of a Prototypical Protonated Pentapeptide: Spectroscopic Evidence for Formation of a Charge-Stabilized β-Hairpin.

  2016cites this paper
• Novel Chemical Tools and Methods for Quantitative Mass Spectrometry-Based Proteomics

  2015cites this paper
• Formation of a1 Ions Directly from Oxazolone b2 Ions: an Energy-Resolved and Computational Study

  2015cites this paper
• Gas-phase structures and proton affinities of N-terminal proline containing b2+ ions from protonated model peptides

  2015cites this paper
• Investigation of bn-44 Peptide Fragments Using High Resolution Mass Spectrometry and Isotope Labeling

  2014cites this paper
• Statistical characterization of HCD fragmentation patterns of tryptic peptides on an LTQ Orbitrap Velos mass spectrometer.

  2014cites this paper
• IR action spectroscopy shows competitive oxazolone and diketopiperazine formation in peptides depends on peptide length and identity of terminal residue in the departing fragment.

  2014cites this paper
• Peptide Dimethylation: Fragmentation Control via Distancing the Dimethylamino Group

  2014cites this paper
• Study on the Fragmentation Pathway of the Aconitine-Type Alkaloids under Electrospray Ionization Tandem Mass Spectrometry Utilizing Quantum Chemistry

  2013cites this paper
• Structures of an* Ions Derived from Protonated Pentaglycine and Pentaalanine: Results from IRMPD Spectroscopy and DFT Calculations

  2013cites this paper
• Influence of N-terminal residue composition on the structure of proline-containing b2+ ions.

  2013cites this paper
• Fragmentation Reactions of Methionine-Containing Protonated Octapeptides and Fragment Ions Therefrom: An Energy-Resolved Study

  2013cites this paper
• Investigation of peptide size, residue position, neighbor amino acid and side chain effect on macrocyclization of bn (n = 5-7) ions

  2012cites this paper
• Occurrence of C-Terminal Residue Exclusion in Peptide Fragmentation by ESI and MALDI Tandem Mass Spectrometry

  2012cites this paper
• Structural influences on preferential oxazolone versus diketopiperazine b(2+) ion formation for histidine analogue-containing peptides.

  2012cites this paper
• Rearrangement Pathways of the a4 Ion of Protonated YGGFL Characterized by IR Spectroscopy and Modeling

  2012cites this paper
• Conformation-Specific Spectroscopy of Peptide Fragment Ions in a Low-Temperature Ion Trap

  2012cites this paper
• Competition between diketopiperazine and oxazolone formation in water loss products from protonated ArgGly and GlyArg

  2012cites this paper
• Sequencing Lys-N Proteolytic Peptides by ESI and MALDI Tandem Mass Spectrometry

  2011cites this paper
• Towards Understanding the Tandem Mass Spectra of Protonated Oligopeptides. 2: The Proline Effect in Collision-Induced Dissociation of Protonated Ala-Ala-Xxx-Pro-Ala (Xxx = Ala, Ser, Leu, Val, Phe, and Trp)

  2011cites this paper
• Role of 2-oxo and 2-thioxo modifications on the fragmentation reactions of the histidine radical cation.

  2011cites this paper
• Aliphatic dipeptide tags for multi-2-plex protein quantification.

  2011cites this paper
• N-Protonated Isomers as Gateways to Peptide Ion Fragmentation

  2011cites this paper
• Structure and Reactivity of a n and a n * Peptide Fragments Investigated Using Isotope Labeling, Tandem Mass Spectrometry, and Density Functional Theory Calculations*

  2011cites this paper
• Role of 2-oxo and 2-thioxo modifications on the proton affinity of histidine and fragmentation reactions of protonated histidine.

  2010cites this paper
• Effect of the basic residue on the energetics, dynamics, and mechanisms of gas-phase fragmentation of protonated peptides.

  2010cites this paper
• Effect of the his residue on the cyclization of b ions

  2010cites this paper
• Sequencing of the thirteen structurally isomeric quartets of N‐terminal dipeptide motifs in peptides by collision‐induced dissociation

  2009cites this paper
• Correct identification of oxidized histidine residues using electron-transfer dissociation.

  2009cites this paper
• Fragmentation of doubly-protonated Pro-His-Xaa tripeptides: Formation of b22+ ions

  2009cites this paper
• Influence of temperature and crown ether complex formation on the charge partitioning between z and c fragments formed after electron capture by small peptide dications

  2009cites this paper
• Fragmentation reactions of some peptide b3 ions: an energy-resolved study.

  2009cites this paper
• Cyclization of peptide b9 ions

  2009cites this paper
• To b or not to b: the ongoing saga of peptide b ions.

  2009cites this paper
• Evidence of diketopiperazine and oxazolone structures for HA b2+ ion.

  2009cites this paper
• Structure and reactivity of an and a*n peptide fragments investigated using isotope labeling, tandem mass spectrometry, and density functional theory calculations

  2008cites this paper
• Peptide sequence scrambling through cyclization of b5 ions

  2008cites this paper
• Fragmentation of protonated dipeptides containing arginine. Effect of activation method

  2007cites this paper
• Comparison of collision-induced dissociation and electron-induced dissociation of singly protonated aromatic amino acids, cystine and related simple peptides using a hybrid linear ion trap–FT-ICR mass spectrometer

  2007cites this paper
• The effect of histidine oxidation on the dissociation patterns of peptide ions

  2007cites this paper
• A study of b1+H2O and b1-ions in the product ion spectra of dipeptides containing N-terminal basic amino acid residues

  2007cites this paper
• Investigation of gas phase ion structure for proline-containing b2 ion

  2006cites this paper
• The fragmentation of protonated tyrosine and iodotyrosines: The effect of substituents on the losses of NH3 and of H2O and CO

  2006cites this paper
• Neutral loss of water from the b ions with histidine at the C-terminus and formation of the c ions involving lysine side chains.

  2006cites this paper
• Using tandem mass spectrometry to predict chemical transformations of 2-pyrimidinyloxy-N-arylbenzyl amine derivatives in solution

  2006cites this paper
• Mechanisms of peptide fragmentation from time- and energy-resolved surface-induced dissociation studies: Dissociation of angiotensin analogs

  2006cites this paper
• The role of the position of the basic residue in the generation and fragmentation of peptide radical cations

  2006cites this paper
• Fragmentation pathways of protonated peptides.

  2005cites this paper
• Structural and sequence effects in the fragmentation of protonated tripeptides containing tyrosine

  2005cites this paper
• Fragmentation of protonated oligoalanines: Amide bond cleavage and beyond

  2004cites this paper
• Fragmentation reactions of protonated peptides containing glutamine or glutamic acid.

  2003cites this paper
• 9 Organic gas phase ion chemistry

  2002cites this paper