ArticleJournal of the American Chemical Society2017
Thiol Specific and Tracelessly Removable Bioconjugation via Michael Addition to 5-Methylene Pyrrolones.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 46 papers.
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Who cites it
46 citing papers in PubMed, 126 citations in OpenAlex.
- Protein-Protein Cross-Linking by a DNA Damage-Derived Histone Modification.Journal of the American Chemical Society · 2026Article
- Traceless linkers used for reversible protein-polymer conjugations.Chemical science · 2026Review
- Tunable Linkers for Dynamic Thiol-Based Bioconjugation Strategies.Biomacromolecules · 2026Review
- Achieving cysteine-selective peptide/protein bioconjugation via tunable triazine-pyridine chemistry.Science advances · 2025Article
- Article
- Electro-induced C-H/S-H cross-coupling for the functionalization/macrocyclization of cysteine-containing peptides.Nature communications · 2025Article
- Diverse reactivity of maleimides in polymer science and beyond.Polymer international · 2025Article
- Novel Maleimide Linkers Based on a Piperazine Motif for Strongly Increased Aqueous Solubility.ACS omega · 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
- Chemoselective Reagents for the Traceless Bioreversible Modification of Native Proteins.Bioconjugate chemistry · 2024Article
- Exploring 2-Sulfonylpyrimidine Warheads as Acrylamide Surrogates for Targeted Covalent Inhibition: A BTK Story.Journal of medicinal chemistry · 2024Article
- Click Chemistry: Reaction Rates and Their Suitability for Biomedical Applications.Bioconjugate chemistry · 2024Review
- Biocompatible strategies for peptide macrocyclisation.Chemical science · 2024Review
- Photo-caged 2-butene-1,4-dial as an efficient, target-specific photo-crosslinker for covalent trapping of DNA-binding proteins.Chemical science · 2023Article
- Structure-Reactivity Studies of 2-Sulfonylpyrimidines Allow Selective Protein Arylation.Bioconjugate chemistry · 2023Article
- Optimization of an alum-anchored clinical HIV vaccine candidate.NPJ vaccines · 2023Article
- Histone Deacetylase 1 Inhibition by Peptides Containing a DNA Damage-Induced, Nonenzymatic, Histone Covalent Modification.Biochemistry · 2023Article
- Light controlled reversible Michael addition of cysteine: a new tool for dynamic site-specific labeling of proteins.The Analyst · 2023Article
- Review
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
5-Methylene pyrrolones (5MPs) are highly thiol-specific and tracelessly removable bioconjugation tools. 5MPs are readily prepared from primary amines in one step. 5MPs exhibit significantly improved stability under physiologically relevant conditions and cysteine specificity compared to commonly used analogues, maleimides. Michael addition of thiol to 5MPs occurs rapidly, cleanly, and does not generate a stereocenter. The conjugates efficiently release thiols via retro-Michael reaction in alkaline buffer (pH 9.5) or via thiol exchange at pH 7.5. This unique property makes 5MPs valuable for the controlled release of conjugated cargo and temporary thiol protection. The utilization of 5MPs for protein immobilization and pull-down of active complexes is illustrated using E. coli. acetohydroxyacid synthase isozyme I.
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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.