ArticleNature communications2016
Aromatic thiol-mediated cleavage of N-O bonds enables chemical ubiquitylation of folded proteins.
Article in Nature communications, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 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
20 citing papers in PubMed, 62 citations in OpenAlex.
- Chemical Ligation of Backbone N-hydroxylated Peptides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Thioether-mediated protein ubiquitination in constructing affinity- and activity-based ubiquitinated protein probes.Nature protocols · 2025Review
- Advances in the chemical synthesis of human proteoforms.Science China. Life sciences · 2025Review
- Circular Engineered Sortase for Interrogating Histone H3 in Chromatin.Journal of the American Chemical Society · 2024Article
- A circular engineered sortase for interrogating histone H3 in chromatin.bioRxiv : the preprint server for biology · 2024Article
- Article
- Signalling mechanisms and cellular functions of SUMO.Nature reviews. Molecular cell biology · 2022Review
- Posttranslational Chemical Mutagenesis Methods to Insert Posttranslational Modifications into Recombinant Proteins.Molecules (Basel, Switzerland) · 2022Review
- Insights in Post-Translational Modifications: Ubiquitin and SUMO.International journal of molecular sciences · 2022Review
- The chemical biology of ubiquitin.Biochimica et biophysica acta. General subjects · 2022Review
- Chemical methods for protein site-specific ubiquitination.RSC chemical biology · 2021Review
- Chemoenzymatic Semisynthesis of Proteins.Chemical reviews · 2020Review
- Facile Semisynthesis of Ubiquitylated Peptides with the Ligation Auxiliary 2-Aminooxyethanethiol.Methods in molecular biology (Clifton, N.J.) · 2020Article
- Auxiliary-assisted chemical ubiquitylation of NEMO and linear extension by HOIP.Communications chemistry · 2019Article
- A clickable glutamine (CliQ) derivative for the traceless reversible modification of peptides and proteins.Chemical communications (Cambridge, England) · 2019Article
- Palladium prompted on-demand cysteine chemistry for the synthesis of challenging and uniquely modified proteins.Nature communications · 2018Article
- A Highly Efficient Synthesis of Polyubiquitin Chains.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2018Article
- Amide-forming chemical ligation viaProceedings of the National Academy of Sciences of the United States of America · 2018Article
- Advancing the Frontiers of Chemical Protein Synthesis-The 7Cell chemical biology · 2018Article
- Exploring chemoselective S-to-N acyl transfer reactions in synthesis and chemical biology.Nature communications · 2017Review
Corrections and comments
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Authors and funding
11 authors at 3 institutions in 2 countries.
Funding
Abstract
Access to protein substrates homogenously modified by ubiquitin (Ub) is critical for biophysical and biochemical investigations aimed at deconvoluting the myriad biological roles for Ub. Current chemical strategies for protein ubiquitylation, however, employ temporary ligation auxiliaries that are removed under harsh denaturing conditions and have limited applicability. We report an unprecedented aromatic thiol-mediated N-O bond cleavage and its application towards native chemical ubiquitylation with the ligation auxiliary 2-aminooxyethanethiol. Our interrogation of the reaction mechanism suggests a disulfide radical anion as the active species capable of cleaving the N-O bond. The successful semisynthesis of full-length histone H2B modified by the small ubiquitin-like modifier-3 (SUMO-3) protein further demonstrates the generalizability and compatibility of our strategy with folded proteins.
Identifiers
What OpenQuestion holds
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.