ArticleNature communications2020
Cysteine-specific protein multi-functionalization and disulfide bridging using 3-bromo-5-methylene pyrrolones.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 35 papers.
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Who cites it
35 citing papers in PubMed.
- Protein-Protein Cross-Linking by a DNA Damage-Derived Histone Modification.Journal of the American Chemical Society · 2026Article
- Disulfide modification and thiol protection via tris(trimethylsilyl)silane-mediated hydrosilylation of disulfides.Nature communications · 2026Article
- Engineering Extended Release Profiles for Biologic Formulations via Chemical Cross-Linking of Poloxamer 407 Hydrogels.ACS omega · 2025Article
- Achieving cysteine-selective peptide/protein bioconjugation via tunable triazine-pyridine chemistry.Science advances · 2025Article
- Electro-induced C-H/S-H cross-coupling for the functionalization/macrocyclization of cysteine-containing peptides.Nature communications · 2025Article
- Article
- Prospects and problems in enzyme immobilization methodology: comprehensive review.Biophysical reviews · 2025Review
- Chemoselective dual functionalization of proteins via 1,6-addition of thiols to trifunctional N-alkylpyridinium.Nature communications · 2025Article
- Green Innovation: Harnessing N-bromosuccinimide as a Versatile Reagent in Organic Synthesis.Current organic synthesis · 2025Article
- An innovative strategy for radical-mediated, bidirectional controlled disulfide exchange.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Target Bioconjugation of Protein Through Chemical, Molecular Dynamics, and Artificial Intelligence Approaches.Metabolites · 2024Review
- Peptide and Protein Cysteine Modification Enabled by Hydrosulfuration of Ynamide.ACS central science · 2024Article
- Chemical Synthesis of Human Proteoforms and Application in Biomedicine.ACS central science · 2024Review
- Facile Access to Branched Multispecific Proteins.Bioconjugate chemistry · 2024Article
- Tracking Inhibition of Human Small C-Terminal Domain Phosphatase 1 Using 193 nm Ultraviolet Photodissociation Mass Spectrometry.Journal of the American Society for Mass Spectrometry · 2024Article
- Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation.Nature chemistry · 2024Article
- 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
- Advances in Biosynthesis of Non-Canonical Amino Acids (ncAAs) and the Methods of ncAAs Incorporation into Proteins.Molecules (Basel, Switzerland) · 2023Review
- Enabling the formation of native mAb, Fab' and Fc-conjugates using a bis-disulfide bridging reagent to achieve tunable payload-to-antibody ratios (PARs).Chemical science · 2023Article
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Authors and funding
8 authors.
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Abstract
Many reagents have been developed for cysteine-specific protein modification. However, few of them allow for multi-functionalization of a single Cys residue and disulfide bridging bioconjugation. Herein, we report 3-bromo-5-methylene pyrrolones (3Br-5MPs) as a simple, robust, and versatile class of reagents for cysteine-specific protein modification. These compounds can be facilely synthesized via a one-pot mild reaction and they show comparable tagging efficiency but higher cysteine specificity than the maleimide counterparts. The addition of cysteine to 3Br-5MPs generates conjugates that are amenable to secondary addition by another thiol or cysteine, making 3Br-5MPs valuable for multi-functionalization of a single cysteine and disulfide bridging bioconjugation. The labeling reaction and subsequent treatments are mild enough to produce stable and active protein conjugates for biological applications.
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