ArticleChemical science2019
Vinylphosphonites for Staudinger-induced chemoselective peptide cyclization and functionalization.
Article in Chemical science, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed, 70 citations in OpenAlex.
- On-resin assembly of cysteine-reactive linkers for controlled site-selective antibody bioconjugation.Nature protocols · 2026Review
- Reflection on "Site-specific PEGylation of proteins by a Staudinger-phosphite reaction": from protein modification to ADCs in the clinic.Chemical science · 2026Article
- Unsaturated Phosphorus Electrophiles to Probe Protein Tyrosine Phosphatases.Angewandte Chemie (International ed. in English) · 2026Article
- Modular Vinyl Phosphonamidates for Cysteine-Directed Protein Targeting.Journal of the American Chemical Society · 2026Article
- Expanding the payload scope in antibody-drug conjugates by delivery of hydroxy-containing drugs through self-immolative phosphoramidates.Nature communications · 2026Article
- Unsaturated Phosphine Oxides for Modular Antibody Rebridging and Single Reagent Peptide-Cyclization-Bioconjugation.Angewandte Chemie (International ed. in English) · 2025Article
- One-Step Maleimide-Based Dual Functionalization of Protein N-Termini.Angewandte Chemie (International ed. in English) · 2025Article
- Peptide macrocyclisationChemical science · 2024Article
- Biocompatible strategies for peptide macrocyclisation.Chemical science · 2024Review
- Design and Evaluation of Phosphonamidate-Linked Exatecan Constructs for Highly Loaded, Stable, and Efficacious Antibody-Drug Conjugates.Molecular cancer therapeutics · 2024Article
- Recent Advances in Bioorthogonal Ligation and Bioconjugation.Topics in current chemistry (Cham) · 2023Review
- The Evolving Landscape of Antibody-Drug Conjugates: In Depth Analysis of Recent Research Progress.Bioconjugate chemistry · 2023Review
- Compact hydrophilic electrophiles enable highly efficacious high DAR ADCs with excellentChemical science · 2023Article
- Fast Cysteine Bioconjugation Chemistry.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- DFT-Guided Discovery of Ethynyl-Triazolyl-Phosphinates as Modular Electrophiles for Chemoselective Cysteine Bioconjugation and Profiling.Angewandte Chemie (International ed. in English) · 2022Article
- A novel β-catenin/BCL9 complex inhibitor blocks oncogenic Wnt signaling and disrupts cholesterol homeostasis in colorectal cancer.Science advances · 2022Article
- Diethynyl Phosphinates for Cysteine-Selective Protein Labeling and Disulfide Rebridging.Angewandte Chemie (International ed. in English) · 2021Article
- Bioorthogonal Reactions of Triarylphosphines and Related Analogues.Chemical reviews · 2021Review
- The mechanism behind enhanced reactivity of unsaturated phosphorus(v) electrophiles towards thiols.Chemical science · 2021Article
- Synthesis and Evaluation of Non-Hydrolyzable Phospho-Lysine Peptide Mimics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In this paper, we introduce vinylphosphonites for chemoselective Staudinger-phosphonite reactions (SPhR) with azides to form vinylphosphonamidates for the subsequent modification of cysteine residues in peptides and proteins. An electron-rich alkene is turned into an electron-deficient vinylphosphonamidate, thereby inducing electrophilic reactivity for a following thiol addition. We show that by varying the phosphonamidate ester substituent we can fine-tune the reactivity of the thiol addition and even control the functional properties of the final conjugate. Furthermore, we observed a drastic increase in thiol addition efficiency when the SPhR is carried out in the presence of a thiol substrate in a one-pot reaction. Hence, we utilize vinylphosphonites for the chemoselective intramolecular cyclization of peptides carrying an azide-containing amino acid and a cysteine in high yields. Our concept was demonstrated for the stapling of a cell-permeable peptidic inhibitor for protein-protein interaction (PPI) between BCL9 and beta-catenin, which is known to create a transcription factor complex playing a role in embryonic development and cancer origin, and for macrocyclization of cell-penetrating peptides (CPPs) to enhance the cellular uptake of proteins.
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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.