ArticleOrganic letters2017
Water-Soluble Palladium Reagents for Cysteine S-Arylation under Ambient Aqueous Conditions.
Article in Organic letters, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed.
- Optimization of a Resolution Process Allowing Access to Both Enantiomers of the Versatile Chiral Phosphine Ligand sSPhos on Scale.Organic process research & development · 2026Article
- Hydrophilic BIPHEPHOS Ligand for Pd-Mediated Cysteine Allylation of Peptides and Proteins in Water.Organic letters · 2025Article
- Organometallic Chemistry Tools for Building Biologically Relevant Nanoscale Systems.Journal of the American Chemical Society · 2024Review
- Organometallic Oxidative Addition Complexes forBioconjugate chemistry · 2024Article
- Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023Review
- Enabling Peptide Ligation at Aromatic Junction Mimics via Native Chemical Ligation and Palladium-Mediated S-Arylation.Organic letters · 2023Article
- Emerging Trends in Cross-Coupling: Twelve-Electron-Based LChemical reviews · 2022Review
- Palladium-peptide oxidative addition complexes for bioconjugation.Chemical science · 2022Article
- An Organometallic Gold(III) Reagent forOrganic letters · 2022Article
- Selective Stepwise Arylation of Unprotected Peptides by PtAngewandte Chemie (International ed. in English) · 2022Article
- Site-Selective Cross-Coupling of Polyhalogenated Arenes and Heteroarenes with Identical Halogen Groups.Chemical reviews · 2022Review
- Palladium-Mediated Incorporation of Carboranes into Small Molecules, Peptides, and Proteins.Journal of the American Chemical Society · 2022Article
- Pd(II)-Mediated C-H Activation for Cysteine Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Peptide stapling by late-stage Suzuki-Miyaura cross-coupling.Beilstein journal of organic chemistry · 2022Article
- A Neophyl Palladacycle as an Air- and Thermally Stable Precursor to Oxidative Addition Complexes.Organic letters · 2021Article
- Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water.Angewandte Chemie (International ed. in English) · 2021Article
- Cleavable and tunable cysteine-specific arylation modification with aryl thioethers.Chemical science · 2021Article
- Amphiphilic Biaryl Monophosphine Ligands by Regioselective Sulfonation.Organic letters · 2021Article
- Synthesis of Hydrophilic Phosphorus Ligands and Their Application in Aqueous-Phase Metal-Catalyzed Reactions.Advanced synthesis & catalysis · 2021Review
- Application of High-Throughput Competition Experiments in the Development of Aspartate-Directed Site-Selective Modification of Tyrosine Residues in Peptides.The Journal of organic chemistry · 2020Article
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Authors and funding
3 authors.
Funding
Abstract
We report the use of a sulfonated biarylphosphine ligand (sSPhos) to promote the chemoselective modification of cysteine containing proteins and peptides with palladium reagents in aqueous medium. The use of sSPhos allowed for the isolation of several air-stable and water-soluble mono- and bis-palladium reagents, which were used in an improved protocol for the rapid S-arylation of cysteines under benign and physiologically relevant conditions. The cosolvent-free aqueous conditions were applied to the conjugation of a variety of biomolecules with affinity tags, heterocycles, fluorophores, and functional handles. Additionally, bis-palladium reagents were used to perform macrocyclization of peptides bearing two cysteine residues.
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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.