ArticleAngewandte Chemie (International ed. in English)2020
Site-Selective Modification of Peptides and Proteins via Interception of Free-Radical-Mediated Dechalcogenation.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Article
- Desulfurative modification of cysteine residues in peptides and proteinsChemical science · 2025Article
- Visible Light Induced Mukaiyama Reagent Promoted Desulfurative Modification of Peptides and Proteins with Nucleotides.ACS central science · 2025Article
- Chemical- and photo-activation of protein-protein thiol-ene coupling for protein profiling.Communications chemistry · 2025Article
- Discovery of a New Class of Aminoacyl Radical Enzymes Expands Nature's Known Radical Chemistry.Journal of the American Chemical Society · 2024Article
- Peptide and Protein Cysteine Modification Enabled by Hydrosulfuration of Ynamide.ACS central science · 2024Article
- Chemical Synthesis of Human Proteoforms and Application in Biomedicine.ACS central science · 2024Review
- Kinetic Resolution of Epimeric Proteins Enables Stereoselective Chemical Mutagenesis.Journal of the American Chemical Society · 2024Article
- Peptide macrocyclisationChemical science · 2024Article
- Photoredox Nucleophilic (Radio)fluorination of Alkoxyamines.Journal of the American Chemical Society · 2024Article
- A pyridinium-based strategy for lysine-selective protein modification and chemoproteomic profiling in live cells.Chemical science · 2024Article
- Carbon-Centered Radicals in Protein Manipulation.ACS central science · 2023Review
- Site-Selective Incorporation of a Functional Group into Lys175 in the Vicinity of the Active Site of Chymotrypsin by Using Peptidyl α-Aminoalkylphosphonate Diphenyl Ester-Derivatives.Molecules (Basel, Switzerland) · 2023Article
- Stereoretentive Post-Translational Protein Editing.ACS central science · 2023Article
- Cysteine-Selective Modification of Peptides and Proteins via Desulfurative C-C Bond Formation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Molecular flavin catalysts for C-H functionalisation and derivatisation of dehydroamino acids.Chemical science · 2022Article
- Site-Selective Installation of NAngewandte Chemie (International ed. in English) · 2022Article
- Site-Selective Modification of Peptides and Proteins via Interception of Free-Radical-Mediated Dechalcogenation.Angewandte Chemie (International ed. in English) · 2020Article
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6 authors.
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Abstract
The development of site-selective chemistry targeting the canonical amino acids enables the controlled installation of desired functionalities into native peptides and proteins. Such techniques facilitate the development of polypeptide conjugates to advance therapeutics, diagnostics, and fundamental science. We report a versatile and selective method to functionalize peptides and proteins through free-radical-mediated dechalcogenation. By exploiting phosphine-induced homolysis of the C-Se and C-S bonds of selenocysteine and cysteine, respectively, we demonstrate the site-selective installation of groups appended to a persistent radical trap. The reaction is rapid, operationally simple, and chemoselective. The resulting aminooxy linker is stable under a variety of conditions and selectively cleavable in the presence of a low-oxidation-state transition metal. We have explored the full scope of this reaction using complex peptide systems and a recombinantly expressed protein.
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