ArticleNature communications2019
Dinitroimidazoles as bifunctional bioconjugation reagents for protein functionalization and peptide macrocyclization.
Article in Nature communications, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 64 citations in OpenAlex.
- Cys-Lys stapling for unprotected peptides via tunable linkers.National science review · 2025Article
- Electro-induced C-H/S-H cross-coupling for the functionalization/macrocyclization of cysteine-containing peptides.Nature communications · 2025Article
- Advances in Peptidomimetics for Next-Generation Therapeutics: Strategies, Modifications, and Applications.Chemical reviews · 2025Review
- Thiol-thiol cross-clicking using bromo-ynone reagents.Nature communications · 2025Article
- Heterobifunctional cross-linker with dinitroimidazole and azide modules for protein and oligonucleotide functionalization.RSC advances · 2025Article
- Peptide and Protein Cysteine Modification Enabled by Hydrosulfuration of Ynamide.ACS central science · 2024Article
- Recent Advances in Metal-Free Peptide Stapling Strategies.Chem & bio engineering · 2024Review
- Cysteine-Specific Multifaceted Bioconjugation of Peptides and Proteins Using 5-Substituted 1,2,3-Triazines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Ultrafast Au(III)-Mediated Arylation of Cysteine.Journal of the American Chemical Society · 2024Article
- Non-symmetric stapling of native peptides.Nature reviews. Chemistry · 2024Review
- Optimization of an alum-anchored clinical HIV vaccine candidate.NPJ vaccines · 2023Article
- Two birds one stone: β-fluoropyrrolyl-cysteine SChemical science · 2023Article
- Fast Cysteine Bioconjugation Chemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Bioconjugation Strategies for Connecting Proteins to DNA-Linkers for Single-Molecule Force-Based Experiments.Nanomaterials (Basel, Switzerland) · 2021Review
- Macrocyclization strategies for cyclic peptides and peptidomimetics.RSC medicinal chemistry · 2021Review
- The mechanism behind enhanced reactivity of unsaturated phosphorus(v) electrophiles towards thiols.Chemical science · 2021Article
- 5-Hydroxy-pyrrolone based building blocks as maleimide alternatives for protein bioconjugation and single-site multi-functionalization.Chemical science · 2021Article
- Cleavable and tunable cysteine-specific arylation modification with aryl thioethers.Chemical science · 2021Article
- Modulating Protein-Protein Interactions by Cyclic and Macrocyclic Peptides. Prominent Strategies and Examples.Molecules (Basel, Switzerland) · 2021Review
- Light-induced primary amines and o-nitrobenzyl alcohols cyclization as a versatile photoclick reaction for modular conjugation.Nature communications · 2020Article
Corrections and comments
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Efficient and site-specific chemical modification of proteins under physiological conditions remains a challenge. Here we report that 1,4-dinitroimidazoles are highly efficient bifunctional bioconjugation reagents for protein functionalization and peptide macrocyclization. Under acidic to neutral aqueous conditions, 1,4-dinitroimidazoles react specifically with cysteines via a cine-substitution mechanism, providing rapid, stable and chemoselective protein bioconjugation. On the other hand, although unreactive towards amine groups under neutral aqueous conditions, 1,4-dinitroimidazoles react with lysines in organic solvents in the presence of base through a ring-opening & ring-close mechanism. The resulting cysteine- and lysine-(4-nitroimidazole) linkages exhibit stability superior to that of commonly employed maleimide-thiol conjugates. We demonstrate that 1,4-dinitroimidazoles can be applied in site-specific protein bioconjugation with functionalities such as fluorophores and bioactive peptides. Furthermore, a bisfunctional 1,4-dinitroimidazole derivative provides facile access to peptide macrocycles by crosslinking a pair of cysteine or lysine residues, including bicyclic peptides of complex architectures through highly controlled consecutive peptide macrocyclization.
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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.