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

共 50 条

[1] In Situ Generation of Fluorescent Amino Acids and Peptides via Double C-H Activation/Annulation
Song, Liangliang
Zhang, Zhefan
Lv, Zhenwei
Xu, Jinyuan
Zhan, Mengru
Tang, Shuo
Li, Huanhuan
Wang, Nanxi
Cai, Lingchao
ACS CATALYSIS, 2023, 13 (20) : 13569 - 13576
[2] Rh(III)-Catalyzed C-H Activation/Annulation for the Construction of Quinolizinones and Indolizines
Hou, Xinjiao
Wang, Run
Fang, Feifei
Qu, Zhiyan
Zhou, Jianhui
Yu, Ting
Wang, Dechuan
Liu, Hong
Zhou, Yu
ORGANIC LETTERS, 2024, 26 (21) : 4451 - 4456
[3] Rhodium(III)-Catalyzed C-H Activation: Annulation of Petrochemical Feedstocks for the Construction of Isoquinolone Scaffolds
Barber, Joyann S.
Kong, Dehuan
Li, Wei
McAlpine, Indrawan J.
Nair, Sajiv K.
Sakata, Sylvie K.
Sun, Nicole
Patman, Ryan L.
SYNLETT, 2021, 32 (02) : 202 - 206
[4] Synthesis and characterisation of novel fluorescent imides by a rhodium(III)-catalysed C-H activation/annulation cascade
Webb, Nicola J.
Fisher, Brittany
Pask, Christopher M.
Watt, Michael S.
Raw, Steven A.
Marsden, Stephen P.
ARKIVOC, 2024,
[5] Construction of Peptide-Isoquinolone Conjugates via Rh(III)- Catalyzed C-H Activation/Annulation
Song, Liangliang
Lv, Zhenwei
Li, Yan
Zhang, Kui
Van der Eycken, Erik V.
Cai, Lingchao
ORGANIC LETTERS, 2023, 25 (17) : 2996 - 3000
[6] Multifunctional Fluorescent Main-Chain Charged Polyelectrolytes Synthesized by Cascade C-H Activation/Annulation Polymerizations
Wang, Kang
Liu, Junkai
Liu, Peiying
Wang, Dong
Han, Ting
Tang, Ben Zhong
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, : 4208 - 4220
[7] Synthesis of Fluorescent 4-Azapyrenes by Palladium(II)-Catalyzed Dual C-H Bond Activation and Annulation
Hsiao, Huan-Chang
Annamalai, Pratheepkumar
Jayakumar, Jayachandran
Sun, Shang-You
Chuang, Shih-Ching
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (06) : 1695 - 1701
[8] Multifunctional Fluorescent Main-Chain Charged Polyelectrolytes Synthesized by Cascade C-H Activation/Annulation Polymerizations
Wang, Kang
Liu, Junkai
Liu, Peiying
Wang, Dong
Han, Ting
Tang, Ben Zhong
Journal of the American Chemical Society, 2023, 145 (07) : 4208 - 4220
[9] Construction of Pyrrolocoumarin Cores through Double C-H Annulation Cascade
Michikita, Ryudai
Usuki, Yoshinosuke
Satoh, Tetsuya
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (22)
[10] Annulation of aromatic Imines via directed C-H bond activation
Thalji, RK
Ahrendt, KA
Bergman, RG
Ellman, JA
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6775 - 6781

← 1 2 3 4 5 →