ArticleProceedings of the National Academy of Sciences of the United States of America2014
Efficient and directed peptide bond formation in the gas phase via ion/ion reactions.
Article in Proceedings of the National Academy of Sciences of the United States of America, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Sequencing of Phosphopeptides Using a Sequential Charge Inversion Ion/Ion Reaction and Electron Capture Dissociation Workflow.Journal of the American Society for Mass Spectrometry · 2024Article
- Aqueous microdroplets enable abiotic synthesis and chain extension of unique peptide isomers from free amino acids.Proceedings of the National Academy of Sciences of the United States of America · 2022Article
- Article
- Polypeptide formation in clusters of β-alanine amino acids by single ion impact.Nature communications · 2020Article
- 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
- Photodissociative Cross-Linking of Non-covalent Peptide-Peptide Ion Complexes in the Gas Phase.Journal of the American Society for Mass Spectrometry · 2018Article
- Study of In-Trap Ion Clouds by Ion Trajectory Simulations.Journal of the American Society for Mass Spectrometry · 2018Article
- The Role of Electron Transfer Dissociation in Modern Proteomics.Analytical chemistry · 2018Review
- Cooperative Formation of Icosahedral Proline Clusters from Dimers.Journal of the American Society for Mass Spectrometry · 2018Article
- Focus on Bio-Ion Chemistry: Interactions of Biological Ions with Ions, Molecules, Surfaces, Electrons, and Light, Honoring Scott A. McLuckey, Recipient of the 2016 ASMS Award for a Distinguished Contribution in Mass Spectrometry.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
- Selective Gas-Phase Oxidation and Localization of Alkylated Cysteine Residues in Polypeptide Ions via Ion/Ion Chemistry.Journal of proteome research · 2016Article
- Efficient Covalent Bond Formation in Gas-Phase Peptide-Peptide Ion Complexes with the Photoleucine Stapler.Journal of the American Society for Mass Spectrometry · 2016Article
- 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
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Authors and funding
2 authors.
Funding
Abstract
Amide linkages are among the most important chemical bonds in living systems, constituting the connections between amino acids in peptides and proteins. We demonstrate the controlled formation of amide bonds between amino acids or peptides in the gas phase using ion/ion reactions in a mass spectrometer. Individual amino acids or peptides can be prepared as reagents by (i) incorporating gas phase-labile protecting groups to silence otherwise reactive functional groups, such as the N terminus; (ii) converting the carboxyl groups to the active ester of N-hydroxysuccinimide; and (iii) incorporating a charge site. Protonation renders basic sites (nucleophiles) unreactive toward the N-hydroxysuccinimide ester reagents, resulting in sites with the greatest gas phase basicities being, in large part, unreactive. The N-terminal amines of most naturally occurring amino acids have lower gas phase basicities than the side chains of the basic amino acids (i.e., those of histidine, lysine, or arginine). Therefore, reagents may be directed to the N terminus of an existing "anchor" peptide to form an amide bond by protonating the anchor peptide's basic residues, while leaving the N-terminal amine unprotonated and therefore reactive. Reaction efficiencies of greater than 30% have been observed. We propose this method as a step toward the controlled synthesis of peptides in the gas phase.
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