ArticleNature communications2018
Palladium prompted on-demand cysteine chemistry for the synthesis of challenging and uniquely modified proteins.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 34 papers.
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Who cites it
34 citing papers in PubMed, 118 citations in OpenAlex.
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- Ruthenium-Catalyzed One-pot Peptide Ligation.Methods in molecular biology (Clifton, N.J.) · 2025Article
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- Location-agnostic site-specific protein bioconjugation via Baylis Hillman adducts.Nature communications · 2024Article
- Synthesis of ubiquitinated proteins for biochemical and functional analysis.Chemical science · 2023Review
- The semisynthesis of site-specifically modified histones and histone-based probes of chromatin-modifying enzymes.Methods (San Diego, Calif.) · 2023Article
- Enabling Peptide Ligation at Aromatic Junction Mimics via Native Chemical Ligation and Palladium-Mediated S-Arylation.Organic letters · 2023Article
- Total synthesis of interleukin-2Chemical science · 2023Article
- Selective macrocyclic peptide modulators of Lys63-linked ubiquitin chains disrupt DNA damage repair.Nature communications · 2022Article
- Posttranslational Chemical Mutagenesis Methods to Insert Posttranslational Modifications into Recombinant Proteins.Molecules (Basel, Switzerland) · 2022Review
- Chemical synthesis of human selenoprotein F and elucidation of its thiol-disulfide oxidoreductase activity.Chemical science · 2022Article
- Improved Handling of Peptide Segments Using Side Chain-Based "Helping Hand" Solubilizing Tools.Methods in molecular biology (Clifton, N.J.) · 2022Article
- Traceless Click-Assisted Native Chemical Ligation Enabled by Protecting Dibenzocyclooctyne from Acid-Mediated Rearrangement with Copper(I).Bioconjugate chemistry · 2021Article
- Parallel Automated Flow Synthesis of Covalent Protein Complexes That Can Inhibit MYC-Driven Transcription.ACS central science · 2021Article
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
Organic chemistry allows for the modification and chemical preparation of protein analogues for various studies. The thiolate side chain of the Cys residue has been a key functionality in these ventures. In order to generate complex molecular targets, there is a particular need to incorporate orthogonal protecting groups of the thiolated amino acids to control the directionality of synthesis and modification site. Here, we demonstrate the tuning of palladium chemoselectivity in aqueous medium for on-demand deprotection of several Cys-protecting groups that are useful in protein synthesis and modification. These tools allow the preparation of highly complex analogues as we demonstrate in the synthesis of the copper storage protein and selectively modified peptides with multiple Cys residues. We also report the synthesis of an activity-based probe comprising ubiquitinated histone H2A and its incorporation into nucleosomes and demonstrate its reactivity with deubiquitinating enzyme to generate a covalent nucleosome-enzyme complex.
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