ArticleChemical science2015
Mechanisms and energetics of free radical initiated disulfide bond cleavage in model peptides and insulin by mass spectrometry.
Article in Chemical science, 2015. 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, 38 citations in OpenAlex.
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- Sensitive Fluorescence Quantitation and Efficient Free Radical Characterization ofAnalytical chemistry · 2025Article
- Free Radical-Based Sequencing for Native Top-Down Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2022Article
- Electrocatalytic Depolymerization of Self-Immolative Poly(Dithiothreitol) Derivatives.Molecules (Basel, Switzerland) · 2022Article
- New free radical-initiated peptide sequencing (FRIPS) mass spectrometry reagent with high conjugation efficiency enabling single-step peptide sequencing.Scientific reports · 2022Article
- Improved gene delivery to K-562 leukemia cells by lipoic acid modified block copolymer micelles.Journal of nanobiotechnology · 2021Article
- Free-Radical-Mediated Glycan Isomer Differentiation.Analytical chemistry · 2020Article
- Two-step reaction mechanism reveals new antioxidant capability of cysteine disulfides against hydroxyl radical attack.Proceedings of the National Academy of Sciences of the United States of America · 2020Article
- Synthesis of poly(disulfide)s with narrow molecular weight distributionsChemical science · 2020Article
- Resin and Magnetic Nanoparticle-Based Free Radical Probes for Glycan Capture, Isolation, and Structural Characterization.Analytical chemistry · 2019Article
- Dandelion flower-like micelles.Chemical science · 2019Article
- Synthesis of New S-S and C-C Bonds by Photoinitiated Radical Recombination Reactions in the Gas Phase.International journal of mass spectrometry · 2019Article
- Free Radical-Initiated Peptide Sequencing Mass Spectrometry for Phosphopeptide Post-translational Modification Analysis.Journal of the American Society for Mass Spectrometry · 2019Article
- Development of Novel Free Radical Initiated Peptide Sequencing Reagent: Application to Identification and Characterization of Peptides by Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2019Article
- Detection of Neutral CO Lost During Ionic Dissociation Using Atmospheric Pressure Thermal Dissociation Mass Spectrometry (APTD-MS).Journal of the American Society for Mass Spectrometry · 2018Article
- Radical Anions of Oxidized vs. Reduced Oxytocin: Influence of Disulfide Bridges on CID and Vacuum UV Photo-Fragmentation.Journal of the American Society for Mass Spectrometry · 2018Article
- Characterization of Disulfide Linkages in Proteins by 193 nm Ultraviolet Photodissociation (UVPD) Mass Spectrometry.Analytical chemistry · 2018Article
- A Click Chemistry-Based Proteomic Approach Reveals that 1,2,4-Trioxolane and Artemisinin Antimalarials Share a Common Protein Alkylation Profile.Angewandte Chemie (International ed. in English) · 2016Article
- A Click Chemistry-Based Proteomic Approach Reveals that 1,2,4-Trioxolane and Artemisinin Antimalarials Share a Common Protein Alkylation Profile.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2016Article
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Authors and funding
6 authors at 3 institutions in 1 country.
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Abstract
We investigate the mechanism of disulfide bond cleavage in gaseous peptide and protein ions initiated by a covalently-attached regiospecific acetyl radical using mass spectrometry (MS). Highly selective S-S bond cleavages with some minor C-S bond cleavages are observed by a single step of collisional activation. We show that even multiple disulfide bonds in intact bovine insulin are fragmented in the MS2 stage, releasing the A- and B-chains with a high yield, which has been challenging to achieve by other ion activation methods. Yet, regardless of the previous reaction mechanism studies, it has remained unclear why (1) disulfide bond cleavage is preferred to peptide backbone fragmentation, and why (2) the S-S bond that requires the higher activation energy conjectured in previously suggested mechanisms is more prone to be cleaved than the C-S bond by hydrogen-deficient radicals. To probe the mechanism of these processes, model peptides possessing deuterated β-carbon(s) at the disulfide bond are employed. It is suggested that the favored pathway of S-S bond cleavage is triggered by direct acetyl radical attack at sulfur with concomitant cleavage of the S-S bond (S
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