ArticleJournal of the American Chemical Society2022
Gold(I)-Mediated Rapid Cyclization of Propargylated Peptides via Imine Formation.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 19 citations in OpenAlex.
- Macrocyclization of native peptides through (thio)urea crosslinking of two amines.Nature communications · 2026Article
- Organometallic Chemistry Approach to Peptide Tricycles.Bioconjugate chemistry · 2026Article
- Rate-Tunable, Metal-Mediated Amide Bond Cleavage for the Controlled Release of Pharmaceuticals.Journal of the American Chemical Society · 2025Article
- Backbone Protecting Groups for Enhanced Peptide and Protein Synthesis.Angewandte Chemie (International ed. in English) · 2025Review
- Metallo-azapeptides: Controlled Metal Chelation to Peptide Backbone Nitrogen.Journal of the American Chemical Society · 2025Article
- Synthesis of Fluorescent Cyclic Peptides via Gold(I)-Catalyzed Macrocyclization.Journal of the American Chemical Society · 2023Article
- Metal-Mediated, Autolytic Amide Bond Cleavage: A Strategy for the Selective, Metal Complexation-Catalyzed, Controlled Release of Metallodrugs.Journal of the American Chemical Society · 2023Article
- Cyclic Peptides in Pipeline: What Future for These Great Molecules?Pharmaceuticals (Basel, Switzerland) · 2023Review
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In fundamental research and drug discovery, there is still a need for effective and straightforward chemical approaches for generating cyclic peptides. The divergent synthesis of cyclic peptides remains a challenge, in particular when cyclization is carried out in the presence of unprotected side chains and a nonpeptidic component within the cycle is needed. Herein, we describe a novel and efficient strategy based on Au(I)-mediated cyclization of unprotected peptides through rapid (30-60 min) amine addition on a propargyl group to generate an imine linkage. Mechanistic insights reveal that the reaction proceeds via regioselective Markovnikov's addition of the amine on the Au(I)-activated propargyl. This strategy was successfully applied to prepare efficiently (56-94%) over 35 diverse cyclic peptides having different sequences and lengths. We have also achieved stereoselective reduction of cyclic imines employing chiral ligands. The practicality of our method was extended for the synthesis of cyclic peptides that bind Lys48-linked di-ubiquitin chains with high affinity, leading to apoptosis of cancer cells.
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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.