ArticleOrganic & biomolecular chemistry2018
Fast, irreversible modification of cysteines through strain releasing conjugate additions of cyclopropenyl ketones.
Article in Organic & biomolecular chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Side-by-Side Comparison of Different Thiol Bioconjugation Strategies for the Chemoselective Radiolabeling of Human Serum Albumin with Zirconium-89.ACS bio & med chem Au · 2026Article
- Site-Selective Peptide and Protein Functionalization with Cyclopropenium Cations.Angewandte Chemie (International ed. in English) · 2025Article
- Generation and Use of Cyclopropenyllithium under Continuous Flow Conditions.Organic letters · 2025Article
- On-Demand Thio-Succinimide Hydrolysis for the Assembly of Stable Protein-Protein Conjugates.Journal of the American Chemical Society · 2024Article
- Cysteine-Specific Multifaceted Bioconjugation of Peptides and Proteins Using 5-Substituted 1,2,3-Triazines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Kinetic models towards an enhanced understanding of diverse ADC conjugation reactions.Frontiers in bioengineering and biotechnology · 2024Article
- A Cysteine-Directed Proximity-Driven Crosslinking Method for Native Peptide Bicyclization.Angewandte Chemie (International ed. in English) · 2023Article
- Compact hydrophilic electrophiles enable highly efficacious high DAR ADCs with excellentChemical science · 2023Article
- Fast Cysteine Bioconjugation Chemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- The mechanism behind enhanced reactivity of unsaturated phosphorus(v) electrophiles towards thiols.Chemical science · 2021Article
- Rational Design of Antigen Incorporation Into Subunit Vaccine Biomaterials Can Enhance Antigen-Specific Immune Responses.Frontiers in immunology · 2020Article
- Metal-Templated Assembly of Cyclopropane-Fused Diazepanones and Diazecanones via exo- trig Nucleophilic Cyclization of Cyclopropenes with Tethered Carbamates.The Journal of organic chemistry · 2018Article
- Lipidated cyclopropenesTetrahedron letters · 2018Article
- Achieving Controlled Biomolecule-Biomaterial Conjugation.Chemical reviews · 2018Review
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7 authors.
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Abstract
A method of cysteine alkylation using cyclopropenyl ketones is described. Due to the significant release of cyclopropene strain energy, reactions of thiols with cyclopropenyl ketones are both fast and irreversible and give rise to stable conjugate addition adducts. The resulting cyclopropenyl ketones have a low molecular weight and allow for simple attachment of amides via N-hydroxysuccinimide (NHS)-esters. While cyclopropenyl ketones do display slow background reactivity toward water, labeling by thiols is much more rapid. The reaction of a cyclopropenyl ketone with glutathione (GSH) proceeds with a rate of 595 M
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