ArticleChembiochem : a European journal of chemical biology2014
Facile synthesis of native and protease-resistant ubiquitylated peptides.
Article in Chembiochem : a European journal of chemical biology, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed, 51 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
- Photocatalytic Diselenide Contraction as a Tool for Site-Selective Isosteric Ubiquitylation.Journal of peptide science : an official publication of the European Peptide Society · 2025Article
- Article
- The semisynthesis of site-specifically modified histones and histone-based probes of chromatin-modifying enzymes.Methods (San Diego, Calif.) · 2023Article
- Semisynthetic Approach to the Analysis of Tumor Suppressor PTEN Ubiquitination.Journal of the American Chemical Society · 2023Article
- The chemical biology of ubiquitin.Biochimica et biophysica acta. General subjects · 2022Review
- Article
- Chemical methods for protein site-specific ubiquitination.RSC chemical biology · 2021Review
- Development and application of ubiquitin-based chemical probes.Chemical science · 2020Review
- Protein Engineering in the Ubiquitin System: Tools for Discovery and Beyond.Pharmacological reviews · 2020Review
- 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
- 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
- Studies of biochemical crosstalk in chromatin with semisynthetic histones.Current opinion in chemical biology · 2018Review
- Amide-forming chemical ligation viaProceedings of the National Academy of Sciences of the United States of America · 2018Article
- Chemically Sumoylated Histone H4 Stimulates Intranucleosomal Demethylation by the LSD1-CoREST Complex.ACS chemical biology · 2017Article
- Biological and Physicochemical Functions of Ubiquitylation Revealed by Synthetic Chemistry Approaches.International journal of molecular sciences · 2017Review
- A Facile N-Mercaptoethoxyglycinamide (MEGA) Linker Approach to Peptide Thioesterification and Cyclization.Journal of the American Chemical Society · 2017Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The reversible post-translational modification of eukaryotic proteins by ubiquitin regulates key cellular processes including protein degradation and gene transcription. Studies of the mechanistic roles for protein ubiquitylation require quantities of homogenously modified substrates that are typically inaccessible from natural sources or by enzymatic ubiquitylation in vitro. Therefore, we developed a facile and scalable methodology for site-specific chemical ubiquitylation. Our semisynthetic strategy utilized a temporary ligation auxiliary, 2-(aminooxy)ethanethiol, to direct ubiquitylation to specific lysine residues in peptide substrates. Mild reductive removal of the auxiliary after ligation yielded ubiquitylated peptides with the native isopeptide linkage. Alternatively, retention of the ligation auxiliary yielded protease-resistant analogues of ubiquitylated peptides. Importantly, our strategy was fully compatible with the presence of protein thiol groups, as demonstrated by the synthesis of peptides modified by the human small ubiquitin-related modifier 3 protein.
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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.