ArticleJournal of the American Society for Mass Spectrometry2012
Solution versus gas-phase modification of peptide cations with NHS-ester reagents.
Article in Journal of the American Society for Mass Spectrometry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
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- Ion Mobility Mass Spectrometry for Large Synthetic Molecules: Expanding the Analytical Toolbox.Journal of the American Chemical Society · 2024Review
- Comparison of Physical Adsorption and Covalent Coupling Methods for Surface Density-Dependent Orientation of Antibody on Silicon.Molecules (Basel, Switzerland) · 2022Article
- Enlisting a Traditional Chinese Medicine to tune the gelation kinetics of a bioactive tissue adhesive for fast hemostasis or minimally invasive therapy.Bioactive materials · 2021Article
- The Vaccinia virion: Filling the gap between atomic and ultrastructure.PLoS pathogens · 2019Article
- Reactive Landing of Gramicidin S and Ubiquitin Ions onto Activated Self-Assembled Monolayer Surfaces.Journal of the American Society for Mass Spectrometry · 2017Article
- Click Addition of a DNA Thread to the N-Termini of Peptides for Their Translocation through Solid-State Nanopores.ACS nano · 2015Article
- 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
- 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
- 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
- Efficient and directed peptide bond formation in the gas phase via ion/ion reactions.Proceedings of the National Academy of Sciences of the United States of America · 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 ion/ion reactions of peptides and proteins: acid/base, redox, and covalent chemistries.Chemical communications (Cambridge, England) · 2013Article
- Gas-phase reactivity of carboxylic acid functional groups with carbodiimides.Journal of the American Society for Mass Spectrometry · 2013Article
- Gas-phase conjugation to arginine residues in polypeptide ions via N-hydroxysuccinimide ester-based reagent ions.Journal of the American Chemical Society · 2012Article
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3 authors.
Funding
Abstract
A comparison between solution and gas phase modification of primary amine sites in model peptide cations with N-hydroxysuccinimide (NHS) ester reagents is presented. In all peptides, the site of modification in solution was directed to the N-terminus by conducting reactions at pH=5, whereas for the same peptides, a lysine residue was preferentially modified in the gas phase. The difference in pKa values of the N-terminus and ε-amino group of the lysine allows for a degree of control over sites of protonation of the peptides in aqueous solution. With removal of the dielectric and multiple charging of the peptide ions in the gas phase, the accommodation of excess charge can affect the preferred sites of reaction. Interaction of the lone pair of the primary nitrogen with a proton reduces its nucleophilicity and, as a result, its reactivity towards NHS-esters. While no evidence for reaction of the N-terminus with sulfo-NHS-acetate was noted in the model peptide cations, a charge inversion experiment using bis[sulfosuccinimidyl] suberate, a cross-linking reagent with two sulfo-NHS-ester functionalities, showed modification of the N-terminus. Hence, an unprotonated N-terminus can serve as a nucleophile to displace NHS, which suggests that its lack of reactivity with the peptide cations is likely due to the participation of the N-terminus in solvating excess charge.
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