ArticleAngewandte Chemie (International ed. in English)2021
Dichloro Butenediamides as Irreversible Site-Selective Protein Conjugation Reagent.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 22 citations in OpenAlex.
- Article
- Toward Precision Bioconjugation: Chemical Strategies for Site-Selective Cysteine Conjugation.Precision chemistry · 2026Review
- Inhibiting Mrt4-rRNA interaction with fumaramidmycin-based derivatives as an antifungal strategy.Nature communications · 2026Article
- Advances in Proximity-Assisted Bioconjugation.Accounts of chemical research · 2025Review
- A simple method for developing lysine targeted covalent protein reagents.Nature communications · 2023Article
- Fast Cysteine Bioconjugation Chemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- OrganometallicBioconjugate chemistry · 2022Article
- Single Mutation on Trastuzumab Modulates the Stability of Antibody-Drug Conjugates Built Using Acetal-Based Linkers and Thiol-Maleimide Chemistry.Journal of the American Chemical Society · 2022Article
- Dichloro Butenediamides as Irreversible Site-Selective Protein Conjugation Reagent.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
8 authors at 5 institutions in 6 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We describe maleic-acid derivatives as robust cysteine-selective reagents for protein labelling with comparable kinetics and superior stability relative to maleimides. Diamide and amido-ester derivatives proved to be efficient protein-labelling species with a common mechanism in which a spontaneous cyclization occurs upon addition to cysteine. Introduction of chlorine atoms in their structures triggers ring hydrolysis or further conjugation with adjacent residues, which results in conjugates that are completely resistant to retro-Michael reactions in the presence of biological thiols and human plasma. By controlling the microenvironment of the reactive site, we can control selectivity towards the hydrolytic pathway, forming homogeneous conjugates. The method is applicable to several scaffolds and enables conjugation of different payloads. The synthetic accessibility of these reagents and the mild conditions required for fast and complete conjugation together with the superior stability of the conjugates make this strategy an important alternative to maleimides in bioconjugation.
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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.