ArticleJournal of the American Chemical Society2019
A Physical Organic Approach to Tuning Reagents for Selective and Stable Methionine Bioconjugation.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 90 citations in OpenAlex.
- Exploring the Potential of Ultrafast Arylation for Capping Cysteine Residues with Fixed Charge Modifications.Journal of the American Society for Mass Spectrometry · 2026Article
- Recent Advances in Bioconjugation of Aromatic Amino Acid Residues by a Reactivity-Guided Approach.Chemical record (New York, N.Y.) · 2026Review
- Site-specific labelling of native peptides and proteins: chemical and enzymatic strategies.Beilstein journal of organic chemistry · 2026Review
- Profiling the proteome-wide selectivity of diverse electrophiles.Nature chemistry · 2025Article
- Controlled reversible methionine-selective sulfimidation of peptides.Science advances · 2025Article
- Exploiting thioether reactivity to label mycobacterial glycans.Proceedings of the National Academy of Sciences of the United States of America · 2025Article
- Emerging opportunities for intact and native protein analysis using chemical proteomics.Analytica chimica acta · 2025Review
- Light-Activated Reactivity of Nitrones with Amino Acids and Proteins.Angewandte Chemie (International ed. in English) · 2025Article
- Enantioselective Chan-LamNature catalysis · 2024Article
- Chemical Synthesis of Human Proteoforms and Application in Biomedicine.ACS central science · 2024Review
- Copper(I)-nitrene platform for chemoproteomic profiling of methionine.Nature communications · 2024Article
- Site-SpecificBioconjugate chemistry · 2023Article
- Single-molecule fluorescence methods for protein biomarker analysis.Analytical and bioanalytical chemistry · 2023Review
- Sulfur-Arylation of Sulfenamides via Ullmann-Type Coupling with (Hetero)aryl Iodides.Organic letters · 2023Article
- Synthesis of Sulfilimines Enabled by Copper-CatalyzedJournal of the American Chemical Society · 2023Article
- An Activity-Based Oxaziridine Platform for Identifying and Developing Covalent Ligands for Functional Allosteric Methionine Sites: Redox-Dependent Inhibition of Cyclin-Dependent Kinase 4.Journal of the American Chemical Society · 2022Article
- Article
- Chemical Conjugation to Less Targeted Proteinogenic Amino Acids.Chembiochem : a European journal of chemical biology · 2022Review
- Methionine oxidation activates pyruvate kinase M2 to promote pancreatic cancer metastasis.Molecular cell · 2022Article
- Luminol anchors improve the electrochemical-tyrosine-click labelling of proteins.Chemical science · 2021Article
Corrections and comments
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Authors and funding
8 authors at 3 institutions in 1 country.
Funding
Abstract
We report a data-driven, physical organic approach to the development of new methionine-selective bioconjugation reagents with tunable adduct stabilities. Statistical modeling of structural features described by intrinsic physical organic parameters was applied to the development of a predictive model and to gain insight into features driving the stability of adducts formed from the chemoselective coupling of oxaziridine and methionine thioether partners through Redox Activated Chemical Tagging (ReACT). From these analyses, a correlation between sulfimide stabilities and sulfimide ν (C═O) stretching frequencies was revealed. We exploited the rational gains in adduct stability exposed by this analysis to achieve the design and synthesis of a bis-oxaziridine reagent for peptide stapling. Indeed, we observed that a macrocyclic peptide formed by ReACT stapling at methionine exhibited improved uptake into live cells compared to an unstapled congener, highlighting the potential utility of this unique chemical tool for thioether modification. This work provides a template for the broader use of data-driven approaches to bioconjugation chemistry and other chemical biology applications.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.