ArticleJournal of the American Chemical Society2012
Gas-phase conjugation to arginine residues in polypeptide ions via N-hydroxysuccinimide ester-based reagent ions.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Biomaterial-based extracellular vesicle delivery systems for wound healing: From fabrication to applications.Bioactive materials · 2026Review
- Revealing the Fates of Proteins in the Gas Phase.International journal of mass spectrometry · 2024Article
- Evidence of Gas Phase Glucosyl Transfer and Glycation in the CID/HCD-Spectra of S-Glucosylated Peptides.International journal of molecular sciences · 2024Article
- Selective Schiff base formation via gas-phase ion/ion reactions to enable differentiation of isobaric lipids in imaging mass spectrometry.Analytical and bioanalytical chemistry · 2023Article
- Cationic peptide carriers enable long-term delivery of insulin-like growth factor-1 to suppress osteoarthritis-induced matrix degradation.Arthritis research & therapy · 2022Article
- Perspective on Emerging Mass Spectrometry Technologies for Comprehensive Lipid Structural Elucidation.Analytical chemistry · 2021Article
- Synthesis of New S-S and C-C Bonds by Photoinitiated Radical Recombination Reactions in the Gas Phase.International journal of 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
- Gas-phase rearrangement reaction of Schiff-base-modified peptide ions.Rapid communications in mass spectrometry : RCM · 2018Article
- Enhanced Reactivity in Nucleophilic Acyl Substitution Ion/Ion Reactions Using Triazole-Ester Reagents.Journal of the American Society for Mass Spectrometry · 2017Article
- Selective Covalent Chemistry via Gas-Phase Ion/ion Reactions: An Exploration of the Energy Surfaces Associated with N-Hydroxysuccinimide Ester Reagents and Primary Amines and Guanidine Groups.Journal of the American Society for Mass Spectrometry · 2016Article
- Gas-Phase Amidation of Carboxylic Acids with Woodward's Reagent K Ions.Journal of the American Society for Mass Spectrometry · 2015Article
- Transformation of [M + 2H](2+) Peptide Cations to [M - H](+), [M + H + O](+), and M(+•) Cations via Ion/Ion Reactions: Reagent Anions Derived from Persulfate.Journal of the American Society for Mass Spectrometry · 2015Article
- Strategies for generating peptide radical cations via ion/ion reactions.Journal of mass spectrometry : JMS · 2015Article
- Gas phase reactivity of carboxylates with N-hydroxysuccinimide esters.Journal of the American Society for Mass Spectrometry · 2015Article
- Oxidation of methionine residues in polypeptide ions via gas-phase ion/ion chemistry.Journal of the American Society for Mass Spectrometry · 2014Article
- Gas Phase Dissociation Behavior of Acyl-Arginine Peptides.International journal of mass spectrometry · 2013Article
- Strategies for the Gas Phase Modification of Cationized Arginine via Ion/ion Reactions.International journal of mass spectrometry · 2013Article
- Reagent cluster anions for multiple gas-phase covalent modifications of peptide and protein cations.Journal of the American Society for Mass Spectrometry · 2013Article
- Gas-phase intramolecular protein crosslinking via ion/ion reactions: ubiquitin and a homobifunctional sulfo-NHS ester.Journal of the American Society for Mass Spectrometry · 2013Article
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3 authors.
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Abstract
Gas-phase conjugation to unprotonated arginine side-chains via N-hydroxysuccinimide (NHS) esters is demonstrated through both charge reduction and charge inversion ion/ion reactions. The unprotonated guanidino group of arginine can serve as a strong nucleophile, resulting in the facile displacement of NHS from NHS esters with concomitant covalent modification of the arginine residue. This reactivity is analogous to that observed with unprotonated primary amines such as the N-terminus or ε-amino group of lysine. In solution, however, the arginine residues tend to be protonated at pH values low enough to prevent hydrolysis of NHS esters, which would render them relatively unreactive with NHS esters. This work demonstrates novel means for gas-phase conjugation to arginine side chains in polypeptide ions.
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