Triple C-H Activation/Annulation: In Situ Construction of Fluorescent Peptides

被引：1

作者：

Zhang, Zhefan ^{[1
]}

Wan, Tianyan ^{[2
]}

Quan, Qi ^{[1
]}

Zang, Yiqi ^{[2
]}

Xu, Jinyuan ^{[2
]}

Tang, Shuo ^{[2
]}

Wang, Nanxi ^{[2
]}

Cai, Lingchao ^{[1
]}

Song, Liangliang ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat Fo, Int Innovat Ctr Forest Chem & Mat,Jiangsu Key Lab, Nanjing 210037, Jiangsu, Peoples R China

[2] Nanjing Univ Chinese Med, Sch Pharm, State Key Lab Cultivat Base TCM Qual & Efficacy, Nanjing 210023, Jiangsu, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 50期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1021/acs.orglett.4c04081

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report a Rh(III)-catalyzed triple C-H activation-annulation of Phe-based peptides with alkynes for the preparation of fluorescent peptides. The robustness of this protocol is reflected by a broad substrate scope, high atom- and step-economy, and excellent chemo- and site-selectivity. An in situ generated polycyclic aromatic hydrocarbon carbocation as a fluorophore exhibits good fluorescence properties (maximum emission wavelength up to 628 nm) and low cell cytotoxicity. The synthetic utility of this method is further demonstrated by versatile product applications in bioconjugation with the protein BSA and specifically targeting lysosomes and mitochondria of live mammalian cells.

引用

页码：10915 / 10920

页数：6

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