ArticleJournal of the American Chemical Society2011
Rapid chemoselective bioconjugation through oxidative coupling of anilines and aminophenols.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
18 citing papers in PubMed, 62 citations in OpenAlex.
- Attenuating RNA Viruses with Expanded Genetic Codes to Evoke Adjustable Immune Response in PylRS-tRNACUAPyl Transgenic Mice.Vaccines · 2023Article
- Protein-Based Model for Energy Transfer between Photosynthetic Light-Harvesting Complexes Is Constructed Using a Direct Protein-Protein Conjugation Strategy.Journal of the American Chemical Society · 2023Article
- The viral capsid as novel nanomaterials for drug delivery.Future science OA · 2021Review
- Site-Specific Bioconjugation through Enzyme-Catalyzed Tyrosine-Cysteine Bond Formation.ACS central science · 2020Article
- Synthesis at the interface of virology and genetic code expansion.Current opinion in chemical biology · 2018Review
- Properties of Site-Specifically Incorporated 3-Aminotyrosine in Proteins To Study Redox-Active Tyrosines: Escherichia coli Ribonucleotide Reductase as a Paradigm.Biochemistry · 2018Article
- ortho-Quinones and Analogues Thereof: Highly Reactive Intermediates for Fast and Selective Biofunctionalization.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Review
- Virus-like particles: Next-generation nanoparticles for targeted therapeutic delivery.Bioengineering & translational medicine · 2017Review
- Direct detection of nitrotyrosine-containing proteins using an aniline-based oxidative coupling strategy.Chemical communications (Cambridge, England) · 2016Article
- Synthetically Modified Viral Capsids as Versatile Carriers for Use in Antibody-Based Cell Targeting.Bioconjugate chemistry · 2015Article
- Controlled levels of protein modification through a chromatography-mediated bioconjugation.Chemical science · 2015Article
- Click chemistry in complex mixtures: bioorthogonal bioconjugation.Chemistry & biology · 2014Review
- N-terminal modification of proteins with o-aminophenols.Journal of the American Chemical Society · 2014Article
- Article
- Protein conjugation with genetically encoded unnatural amino acids.Current opinion in chemical biology · 2013Review
- Controlled integration of gold nanoparticles and organic fluorophores using synthetically modified MS2 viral capsids.Journal of the American Chemical Society · 2013Article
- Bioconjugation of green fluorescent protein via an unexpectedly stable cyclic sulfonium intermediate.Chembiochem : a European journal of chemical biology · 2012Article
- Site-specific fluorescent labeling and oriented immobilization of a triple mutant of CYP3A4 via C64.Bioconjugate chemistry · 2012Article
Corrections and comments
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Authors and funding
6 authors at 3 institutions in 1 country.
Funding
Abstract
A highly efficient protein bioconjugation method is described involving addition of anilines to o-aminophenols in the presence of sodium periodate. The reaction takes place in aqueous buffer at pH 6.5 and can reach high conversion in 2-5 min. The major product was characterized using X-ray crystallography, which revealed that an unprecedented oxidative ring contraction occurs after the coupling step. The compatibility of the reaction with protein substrates has been demonstrated through attachment of small molecules, polymer chains, and peptides to p-aminophenylalanine residues introduced into viral capsids through amber stop codon suppression. Coupling of anilines to o-aminophenol groups derived from tyrosine residues is also described. The compatibility of this method with thiol modification chemistry is shown through attachment of a near-IR fluorescent chromophore to cysteine residues inside the viral capsid shells, followed by attachment of integrin-targeting RGD peptides to anilines on the exterior surface.
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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.