ArticleJournal of the American Society for Mass Spectrometry2013
Gas-phase reactivity of carboxylic acid functional groups with carbodiimides.
Article in Journal of the American Society for Mass Spectrometry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Ion-Ion Chemistry for the Analysis of Biomolecular Ions via Tandem Mass Spectrometry: A Tutorial Review.Annual review of analytical chemistry (Palo Alto, Calif.) · 2026Review
- Relative Quantification of Lipid Isomers in Imaging Mass Spectrometry Using Gas-Phase Charge Inversion Ion/Ion Reactions and Infrared Multiphoton Dissociation.Analytical chemistry · 2023Article
- 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
- Perspective on Emerging Mass Spectrometry Technologies for Comprehensive Lipid Structural Elucidation.Analytical chemistry · 2021Article
- Gas-phase rearrangement reaction of Schiff-base-modified peptide ions.Rapid communications in mass spectrometry : RCM · 2018Article
- Design of a TW-SLIM Module for Dual Polarity Confinement, Transport, and Reactions.Journal of the American Society for Mass Spectrometry · 2017Article
- C-terminal peptide extension via gas-phase ion/ion reactions.International journal of mass spectrometry · 2015Article
- Gas-Phase Amidation of Carboxylic Acids with Woodward's Reagent K Ions.Journal of the American Society for Mass Spectrometry · 2015Article
- High-throughput bioconjugation for enhanced 193 nm photodissociation via droplet phase initiated ion/ion chemistry using a front-end dual spray reactor.Analytical chemistry · 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
- Ion/ion reactions with "onium" reagents: an approach for the gas-phase transfer of organic cations to multiply-charged anions.Journal of the American Society for Mass Spectrometry · 2015Article
- Selective removal of alkali metal cations from multiply-charged ions via gas-phase ion/ion reactions using weakly coordinating anions.Journal of the American Society for Mass Spectrometry · 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
- 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 transformation of phosphatidylcholine cations to structurally informative anions via ion/ion chemistry.Analytical chemistry · 2013Article
- Gas-phase ion/ion reactions of peptides and proteins: acid/base, redox, and covalent chemistries.Chemical communications (Cambridge, England) · 2013Article
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Authors and funding
5 authors.
Funding
Abstract
Gas-phase modification of carboxylic acid functionalities is performed via ion/ion reactions with carbodiimide reagents [N-cyclohexyl-N'-(2-morpholinoethyl)carbodiimide (CMC) and [3-(3-Ethylcarbodiimide-1-yl)propyl]trimethylaminium (ECPT)]. Gas-phase ion/ion covalent chemistry requires the formation of a long-lived complex. In this instance, the complex is stabilized by an electrostatic interaction between the fixed charge quaternary ammonium group of the carbodiimide reagent cation and the analyte dianion. Subsequent activation results in characteristic loss of an isocyanate derivative from one side of the carbodiimide functionality, a signature for this covalent chemistry. The resulting amide bond is formed on the analyte at the site of the original carboxylic acid. Reactions involving analytes that do not contain available carboxylic acid groups (e.g., they have been converted to sodium salts) or reagents that do not have the carbodiimide functionality do not undergo a covalent reaction. This chemistry is demonstrated using PAMAM generation 0.5 dendrimer, ethylenediaminetetraacetic acid (EDTA), and the model peptide DGAILDGAILD. This work demonstrates the selective gas-phase covalent modification of carboxylic acid functionalities.
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