ArticleJournal of the American Society for Mass Spectrometry2016
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.
Article in Journal of the American Society for Mass Spectrometry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 31 citations in OpenAlex.
- Analytical applications of gas-phase ion chemistry enabled by mass spectrometry.Analytical methods : advancing methods and applications · 2026Review
- Characterizing the Energy Surfaces of Competing Pathways in Gas-Phase Charge Inversion Ion/Ion Reactions Involving Cationized Lipids and Anionic Diacids.Journal of the American Society for Mass Spectrometry · 2025Article
- Revealing the Fates of Proteins in the Gas Phase.International journal of mass spectrometry · 2024Article
- Structural Elucidation of Ubiquitin via Gas-Phase Ion/Ion Cross-Linking Reactions Using Sodium-Cationized Reagents Coupled with Infrared Multiphoton Dissociation.Analytical chemistry · 2024Article
- Gas-Phase Fragmentation as a Probe of G-Quadruplex Formation.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
- Recent Advances in Gas-phase Ion/Ion Chemistry for Lipid Analysis.Trends in analytical chemistry : TRAC · 2023Article
- Article
- Gas-Phase Covalent Bond Formation via Nucleophilic Substitution: A Dissociation Kinetics Study of Leaving Groups, Isomeric R Groups, and Nucleophilic Sites.Journal of the American Society for Mass Spectrometry · 2022Article
- Gas-Phase Ion-Ion Reactions for Lipid Identification in Biological Tissue Sections.Methods in molecular biology (Clifton, N.J.) · 2022Article
- Experimental Determination of Activation Energies for Covalent Bond Formation via Ion/Ion Reactions and Competing Processes.Journal of the American Society for Mass Spectrometry · 2021Article
- Perspective on Emerging Mass Spectrometry Technologies for Comprehensive Lipid Structural Elucidation.Analytical chemistry · 2021Article
- Ion Mobility and Gas-Phase Covalent Labeling Study of the Structure and Reactivity of Gaseous Ubiquitin Ions Electrosprayed from Aqueous and Denaturing Solutions.Journal of the American Society for Mass Spectrometry · 2020Article
- Recent Developments in Gas-Phase Ion/Ion Reactions for Analytical Mass Spectrometry.Analytical chemistry · 2020Review
- Ion/ion Charge Inversion/Attachment in Conjunction with Dipolar DC Collisional Activation as a Selective Screen for Sulfo- and Phosphopeptides.International journal of mass spectrometry · 2019Article
- Gas-Phase Protein Salt Bridge Stabilities from Collisional Activation and Electron Transfer Dissociation.International journal of mass spectrometry · 2017Article
- Reactive Landing of Gramicidin S and Ubiquitin Ions onto Activated Self-Assembled Monolayer Surfaces.Journal of the American Society for Mass Spectrometry · 2017Article
- Enhanced Reactivity in Nucleophilic Acyl Substitution Ion/Ion Reactions Using Triazole-Ester Reagents.Journal of the American Society for Mass Spectrometry · 2017Article
- Gas-Phase Oxidation of Neutral Basic Residues in Polypeptide Cations by Periodate.Journal of the American Society for Mass Spectrometry · 2016Article
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Selective covalent bond forming reactions (referred to as covalent reactions) can occur in gas-phase ion/ion reactions and take place via the formation of a long-lived chemical complex. The gas-phase ion/ion reactivity between sulfo-N-hydroxysuccinimide (sulfo-NHS) ester reagent anions and peptide cations containing a primary amine or guanidine group has been examined via DFT calculations and complex dissociation rate measurements. The results reveal insights regarding the roles of the barriers of competing processes within the complex. When the covalent reaction is exothermic, two prototypical cases, determined by the nature of the energy surface, are apparent. The product partitioning between covalent reaction and simple proton transfer upon dissociation of the long-lived complex is sensitive to activation conditions when the transition state barrier for covalent reaction is relatively high (case 1) but is insensitive to activation conditions when the transition state barrier is relatively low (case 2). Covalent reaction efficiencies are very high in case 2 scenarios, such as when the reactive site is a guanidine and the anion attachment site is a guanidinium ion. Covalent reaction efficiencies are variable, and generally low, in case 1 scenarios, such as when an amine is the reactive site and an ammonium ion is the site of anion attachment. A relatively long slow-heating step prior to the complex dissociation step, however, can dramatically increase covalent reaction yield in case 1 scenarios. Graphical Abstract ᅟ.
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