ArticleChemical science2022
Direct formation and site-selective elaboration of methionine sulfoximine in polypeptides.
Article in Chemical science, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed, 18 citations in OpenAlex.
- It's a Gas: Bioconjugation With Vapor-Phase Reagents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Methionine-specific nonreversible bioconjugation: Advancing precision protein modification.Proceedings of the National Academy of Sciences of the United States of America · 2026Article
- Controlled reversible methionine-selective sulfimidation of peptides.Science advances · 2025Article
- Copper(I)-nitrene platform for chemoproteomic profiling of methionine.Nature communications · 2024Article
- Synthesis of Sulfoximines and Sulfonimidamides Using Hypervalent Iodine Mediated NH Transfer.Molecules (Basel, Switzerland) · 2023Review
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Sulfoximines are emerging moieties for medicinal and biological chemistry, due in part to their efficacy in selective inhibition of amide-forming enzymes such as γ-glutamylcysteine synthetase. While small-molecule sulfoximines such as methionine sulfoximine (MSO) and its derivatives are well studied, structures with methionine sulfoximine residues within complex polypeptides have been generally inaccessible. This paper describes a straightforward means of late-stage one-step oxidation of methionine residues within polypeptides to afford NH-sulfoximines. We also present chemoselective subsequent elaboration, most notably by copper(ii)-mediated N-H cross-coupling at methionine sulfoximine residues with arylboronic acid reagents. This development serves as a strategy to incorporate diverse sulfoximine structures within natural polypeptides, and also identifies the methionine sulfoximine residue as a new site for bioorthogonal, chemoselective bioconjugation.
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Registered trials
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