Synthesis of Fluorescent Cyclic Peptides via Gold(I)-Catalyzed Macrocyclization
Journal of the American Chemical Society(2023)
摘要
Rapid and efficient cyclization methods that form structurally novel peptidic macrocycles are of high importance for medicinal chemistry. Herein, we report the first gold-(I)-catalyzed macrocyclization of peptide-EBXs (ethynylbenziodoxolones) via C-2-Trp C-H activation. This reaction was carried out in the presence of protecting group free peptide sequences and is enabled by a simple commercial gold catalyst (AuCl center dot Me2S). The method displayed a rapid reaction rate (within 10 min), wide functional group tolerance (27 unprotected peptides were cyclized), and up to 86% isolated yield. The obtained highly conjugated cyclic peptide linker, formed through C-H alkynylation, can be directly applied to live-cell imaging as a fluorescent probe without further attachment of fluorophores.
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