Synthesis of Fluorescent Cyclic Peptides via Gold(I)-Catalyzed Macrocyclization,Journal of the American Chemical Society

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Synthesis of Fluorescent Cyclic Peptides via Gold(I)-Catalyzed Macrocyclization
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-11-30 , DOI: 10.1021/jacs.3c09261
Xing-Yu Liu ₁ , Wei Cai ₂ , Nathan Ronceray ₃ , Aleksandra Radenovic ₃ , Beat Fierz ₂ , Jerome Waser ₁

Affiliation

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 C₂-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·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.

中文翻译：

金(I)催化大环化合成荧光环肽

形成结构新颖的肽大环化合物的快速有效的环化方法对于药物化学非常重要。在此，我们报告了第一个金 (I) 催化的肽-EBX（乙炔基苯并酮）通过 C ₂ -Trp C–H 活化的大环化。该反应在无保护基团的肽序列存在下进行，并通过简单的商业金催化剂（AuCl·Me ₂ S）实现。该方法反应速度快（10 分钟内）、广泛的官能团耐受性（27 个未保护的肽被环化）和高达 86% 的分离收率。通过C-H炔基化形成的高度结合的环肽接头可以作为荧光探针直接应用于活细胞成像，而无需进一步附着荧光团。

更新日期：2023-11-30

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