ArticleJournal of the American Chemical Society2015
An Umpolung Approach for the Chemoselective Arylation of Selenocysteine in Unprotected Peptides.
Article in Journal of the American Chemical Society, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Harnessing the Reactivity of Sulfinate Salts With Cystine: An Umpolung Approach to Residue-Specific Peptide Modification.Angewandte Chemie (International ed. in English) · 2026Article
- Highly selective and AI-predictable Se-N exchange chemistry between benzoselenazolones and boronic acids for programmable, parallel, and DNA-encoded library synthesis.Chemical science · 2026Article
- Late-Stage Aromatic C-H Bond Functionalization for Cysteine/Selenocysteine Bioconjugation.Journal of the American Chemical Society · 2025Article
- Selenium chemistry for spatio-selective peptide and protein functionalization.Nature reviews. Chemistry · 2024Review
- Site-selective photocatalytic functionalization of peptides and proteins at selenocysteine.Nature communications · 2022Article
- Umpolung strategies for the functionalization of peptides and proteins.Chemical science · 2022Review
- Organometallic AlaChem catalysis · 2021Article
- DeaminativeChemical science · 2021Article
- Site-Selective Modification of Peptides and Proteins via Interception of Free-Radical-Mediated Dechalcogenation.Angewandte Chemie (International ed. in English) · 2020Article
- Chemistry and Chemical Biology of Selenenyl Sulfides and Thioseleninic Acids.Antioxidants & redox signaling · 2020Article
- Stereoselective and Divergent Construction of β-Thiolated/Selenolated Amino Acids via Photoredox-Catalyzed Asymmetric Giese Reaction.Journal of the American Chemical Society · 2020Article
- Indolylboronic Acids: Preparation and Applications.Molecules (Basel, Switzerland) · 2019Review
- Palladium-Catalyzed Suzuki-Miyaura Reactions of Aspartic Acid Derived Phenyl Esters.Organic letters · 2019Article
- Arylation Chemistry for Bioconjugation.Angewandte Chemie (International ed. in English) · 2019Review
- A chemoselective strategy for late-stage functionalization of complex small molecules with polypeptides and proteins.Nature chemistry · 2019Article
- Custom selenoprotein production enabled by laboratory evolution of recoded bacterial strains.Nature biotechnology · 2018Article
- A Facile Method for Producing Selenocysteine-Containing Proteins.Angewandte Chemie (International ed. in English) · 2018Article
- [A facile method for producing selenocysteine-containing proteins].Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2018Article
- Residue-Specific Peptide Modification: A Chemist's Guide.Biochemistry · 2017Review
- Insights into the deselenization of selenocysteine into alanine and serine.Chemical science · 2015Article
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Authors and funding
4 authors.
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Abstract
Herein we report an umpolung strategy for the bioconjugation of selenocysteine in unprotected peptides. This mild and operationally simple approach takes advantage of the electrophilic character of an oxidized selenocysteine (Se-S bond) to react with a nucleophilic arylboronic acid to provide the arylated selenocysteine within hours. This reaction is amenable to a wide range of boronic acids with different biorelevant functional groups and is unique to selenocysteine. Experimental evidence indicates that under oxidative conditions the arylated derivatives are more stable than the corresponding alkylated selenocysteine.
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