ArticleChemical science2020
One-pot thiol-amine bioconjugation to maleimides: simultaneous stabilisation and dual functionalisation.
Article in Chemical science, 2020. 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.
- Spontaneous Non-Catalyzed Molecular Reactions and Interactions in the Human Body: Biomedical Implications.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Review
- Electroactive Proteinoid-Quantum Dot Systems.Small science · 2025Article
- Thiol-thiol cross-clicking using bromo-ynone reagents.Nature communications · 2025Article
- Engineering Phages to Fight Multidrug-Resistant Bacteria.Chemical reviews · 2025Review
- Maleimide functionalized polycaprolactone micelles for glutathione quenching and doxorubicin delivery.Chemical science · 2024Article
- Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation.Nature chemistry · 2024Article
- Electrochemical Visualization of Single-Molecule Thiol Substitution with Nanopore Measurement.ACS measurement science au · 2024Article
- Use of pyridazinediones for tuneable and reversible covalent cysteine modification applied to peptides, proteins and hydrogels.Chemical science · 2023Article
- Synthesis and Evaluation of Clinically Translatable Targeted Microbubbles Using a Microfluidic Device for In Vivo Ultrasound Molecular Imaging.International journal of molecular sciences · 2023Article
- Hyaluronic Acid-PEG-Based Diels-AlderBiomacromolecules · 2022Article
- Hydrolytically Stable Maleimide-End-Functionalized Polymers for Site-Specific Protein Conjugation.Bioconjugate chemistry · 2021Article
- Bone Regeneration Using MMP-Cleavable Peptides-Based Hydrogels.Gels (Basel, Switzerland) · 2021Review
- A Plug-and-Play Platform for the Formation of Trifunctional Cysteine Bioconjugates that also Offers Control over Thiol Cleavability.Bioconjugate chemistry · 2021Article
- 5-Hydroxy-pyrrolone based building blocks as maleimide alternatives for protein bioconjugation and single-site multi-functionalization.Chemical science · 2021Article
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
Maleimide chemistry is widely used in the site-selective modification of proteins. However, hydrolysis of the resultant thiosuccinimides is required to provide robust stability to the bioconjugates. Herein, we present an alternative approach that affords simultaneous stabilisation and dual functionalisation in a one pot fashion. By consecutive conjugation of a thiol and an amine to dibromomaleimides, we show that aminothiomaleimides can be generated extremely efficiently. Furthermore, the amine serves to deactivate the electrophilicity of the maleimide, precluding further reactivity and hence generating stable conjugates. We have applied this conjugation strategy to peptides and proteins to generate stabilised trifunctional conjugates. We propose that this stabilisation-dual modification strategy could have widespread use in the generation of diverse conjugates.
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Registered trials
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