ArticleNature chemistry2024
Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation.
Article in Nature chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 23 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
23 citing papers in PubMed, 55 citations in OpenAlex.
- Traceless trimethyl-lock translators for thiol-mediated uptake of native proteins as covalent constructs.Chemical science · 2026Article
- Modular Assembly of Bioconjugates Enabled by a Pyridine-Based Chemoselective Sequential Conjugation Platform.Angewandte Chemie (International ed. in English) · 2026Article
- Harnessing the Reactivity of Sulfinate Salts With Cystine: An Umpolung Approach to Residue-Specific Peptide Modification.Angewandte Chemie (International ed. in English) · 2026Article
- Biocompatible ligand balancing in transition metal coordination enables benign in-cell protein arylation.Nature chemistry · 2026Article
- Article
- Rapid vinyl thianthrenium tetrafluoroborate-promoted thioacid-based native chemical ligation and its applications in chemical protein synthesis.Communications chemistry · 2026Article
- Grafting Cell-Penetrating Poly(disulfide)s to Substrates of Interest: Dynamic Covalent Bioconjugation for Traceless Delivery.Angewandte Chemie (International ed. in English) · 2026Article
- Thianthrenium Chemistry for Identification of Protein-Protein Interactions in Cells.Journal of the American Chemical Society · 2025Article
- A Unified Synthetic Approach to 2-Alkyl Azetidines, Oxetanes, Thietanes and Cyclobutanes from Unactivated Alkenes.Journal of the American Chemical Society · 2025Article
- Achieving cysteine-selective peptide/protein bioconjugation via tunable triazine-pyridine chemistry.Science advances · 2025Article
- Cys-Lys stapling for unprotected peptides via tunable linkers.National science review · 2025Article
- Electro-induced C-H/S-H cross-coupling for the functionalization/macrocyclization of cysteine-containing peptides.Nature communications · 2025Article
- Article
- Late-Stage Aromatic C-H Bond Functionalization for Cysteine/Selenocysteine Bioconjugation.Journal of the American Chemical Society · 2025Article
- Advances in the chemical synthesis of human proteoforms.Science China. Life sciences · 2025Review
- Thiol-thiol cross-clicking using bromo-ynone reagents.Nature communications · 2025Article
- Facile preparation of sulfonium peptide and protein probes for selective crosslinking of methyllysine readers.Chemical science · 2025Article
- Dual-Performing Vinyltetrazine for Rapid, Selective Bioconjugation and Functionalization of Cysteine Proteins.ACS chemical biology · 2025Article
- Peptide and Protein Cysteine Modification Enabled by Hydrosulfuration of Ynamide.ACS central science · 2024Article
- Analytical Methods for Assessing Thiol Antioxidants in Biological Fluids: A Review.Molecules (Basel, Switzerland) · 2024Review
Corrections and comments
- Erratum issued
Authors and funding
21 authors at 5 institutions in 1 country.
Funding
Abstract
Cysteine conjugation is an important tool in protein research and relies on fast, mild and chemoselective reactions. Cysteinyl thiols can either be modified with prefunctionalized electrophiles, or converted into electrophiles themselves for functionalization with selected nucleophiles in an independent step. Here we report a bioconjugation strategy that uses a vinyl thianthrenium salt to transform cysteine into a highly reactive electrophilic episulfonium intermediate in situ, to enable conjugation with a diverse set of bioorthogonal nucleophiles in a single step. The reactivity profile can connect several nucleophiles to biomolecules through a short and stable ethylene linker, ideal for introduction of infrared labels, post-translational modifications or NMR probes. In the absence of reactive exogenous nucleophiles, nucleophilic amino acids can react with the episulfonium intermediate for native peptide stapling and protein-protein ligation. Ready synthetic access to isotopologues of vinyl thianthrenium salts enables applications in quantitative proteomics. Such diverse applications demonstrate the utility of vinyl-thianthrenium-based bioconjugation as a fast, selective and broadly applicable tool for chemical biology.
Indexed as
Identifiers
What OpenQuestion holds
Registered trials
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.