ArticleJournal of the American Chemical Society2018
Palladium Oxidative Addition Complexes for Peptide and Protein Cross-linking.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 41 papers.
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Who cites it
41 citing papers in PubMed, 122 citations in OpenAlex.
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- Cys-Lys stapling for unprotected peptides via tunable linkers.National science review · 2025Article
- Not So Bioorthogonal Chemistry.Journal of the American Chemical Society · 2025Review
- Ligand-Enabled Selective Coupling of MIDA Boronates to Dehydroalanine-Containing Peptides and Proteins.Journal of the American Chemical Society · 2025Article
- Organometallic Chemistry Tools for Building Biologically Relevant Nanoscale Systems.Journal of the American Chemical Society · 2024Review
- Synthesis and Reactivity of Dipalladated Derivatives of Terephthalaldehyde.Organometallics · 2024Article
- Biological activity of a stable 6-aryl-2-benzoyl-pyridine colchicine-binding site inhibitor, 60c, in metastatic, triple-negative breast cancer.Cancer letters · 2024Article
- Another side of side chains.Nature reviews. Chemistry · 2024Article
- Non-symmetric stapling of native peptides.Nature reviews. Chemistry · 2024Review
- Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023Review
- Ultra-rapid Electrophilic Cysteine Arylation.Journal of the American Chemical Society · 2023Article
- Fluorogenic Reactions in Chemical Biology: Seeing Chemistry in Cells.Chemical & biomedical imaging · 2023Review
- A Cysteine-Directed Proximity-Driven Crosslinking Method for Native Peptide Bicyclization.Angewandte Chemie (International ed. in English) · 2023Article
- The thiol-sulfoxonium ylide photo-click reaction for bioconjugation.Chemical science · 2023Article
- Emerging Trends in Cross-Coupling: Twelve-Electron-Based LChemical 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
- Highly Efficient Cyclization Approach of Propargylated Peptides via Gold(I)-Mediated Sequential C-N, C-O, and C-C Bond Formation.ACS central science · 2021Article
- Solid-Phase Peptide Macrocyclization and Multifunctionalization via Dipyrrin Construction.Angewandte Chemie (International ed. in English) · 2021Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
A new method for cysteine-lysine cross-linking in peptides and proteins using palladium oxidative addition complexes is presented. First, a biarylphosphine-supported palladium reagent is used to transfer an aryl group bearing an O-phenyl carbamate substituent to a cysteine residue. Next, this carbamate undergoes chemoselective acyl substitution by a proximal lysine to form a cross-link. The linkage so formed is stable toward acid, base, oxygen, and external thiol nucleophiles. This method was applied to cross-link cysteine with nearby lysines in sortase A*. Furthermore, we used this method for the intermolecular cross-linking between a peptide and a protein based on the p53-MDM2 interaction. These studies demonstrate the potential for palladium-mediated methods to serve as a platform for the development of future cross-linking techniques for peptides and proteins with natural amino acid residues.
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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.