ArticleJournal of the American Chemical Society2021
An Organometallic Strategy for Cysteine Borylation.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed, 53 citations in OpenAlex.
- Article
- Hydrophilic BIPHEPHOS Ligand for Pd-Mediated Cysteine Allylation of Peptides and Proteins in Water.Organic letters · 2025Article
- Vertex Engineering of the Dodecaborate-Based Broadband Membrane Carriers.Inorganic chemistry · 2025Article
- Organometallic Chemistry Tools for Building Biologically Relevant Nanoscale Systems.Journal of the American Chemical Society · 2024Review
- Orthogonal bioconjugation targeting cysteine-containing peptides and proteins using alkyl thianthrenium salts.Nature communications · 2024Article
- Organometallic Oxidative Addition Complexes forBioconjugate chemistry · 2024Article
- A Pd-catalyzed route to carborane-fused boron heterocycles.Chemical science · 2024Article
- Ultrafast Au(III)-Mediated Arylation of Cysteine.Journal of the American Chemical Society · 2024Article
- Synthesis and Structural Characterization ofMolecules (Basel, Switzerland) · 2023Article
- The thiol-sulfoxonium ylide photo-click reaction for bioconjugation.Chemical science · 2023Article
- Palladium-peptide oxidative addition complexes for bioconjugation.Chemical science · 2022Article
- OrganometallicBioconjugate chemistry · 2022Article
- Chemical and Enzymatic Methods for Post-Translational Protein-Protein Conjugation.Journal of the American Chemical Society · 2022Review
- Selective Stepwise Arylation of Unprotected Peptides by PtAngewandte Chemie (International ed. in English) · 2022Article
- Palladium-Mediated Incorporation of Carboranes into Small Molecules, Peptides, and Proteins.Journal of the American Chemical Society · 2022Article
- Fast and Cysteine-Specific Modification of Peptides, Proteins and Bacteriophage Using Chlorooximes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Pd(II)-Mediated C-H Activation for Cysteine Bioconjugation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Ex Vivo and In Vivo Evaluation of Dodecaborate-Based Clusters Encapsulated in Ferumoxytol Nanoparticles.Langmuir : the ACS journal of surfaces and colloids · 2021Article
- ElectrooxidativeChemical science · 2021Article
Corrections and comments
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Authors and funding
8 authors at 3 institutions in 1 country.
Funding
Abstract
Synthetic bioconjugation at cysteine (Cys) residues in peptides and proteins has emerged as a powerful tool in chemistry. Soft nucleophilicity of the sulfur in Cys renders an exquisite chemoselectivity with which various functional groups can be placed onto this residue under benign conditions. While a variety of reactions have been successful at producing Cys-based bioconjugates, the majority of these feature sulfur-carbon bonds. We report Cys-borylation, wherein a benchtop stable Pt(II)-based organometallic reagent can be used to transfer a boron-rich cluster onto a sulfur moiety in unprotected peptides forging a boron-sulfur bond. Cys-borylation proceeds at room temperature and tolerates a variety of functional groups present in complex polypeptides. Further, the bioconjugation strategy can be applied to a model protein modification of Cys-containing DARPin (designed ankyrin repeat protein). The resultant bioconjugates show no additional toxicity compared to their Cys alkyl-based congeners. Finally, we demonstrate how the developed Cys-borylation can enhance the proteolytic stability of the resultant peptide bioconjugates while maintaining the binding affinity to a protein target.
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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.