Late-Stage Peptide Macrocyclization by Palladium-Catalyzed Site-Selective C-H Olefination of Tryptophan

被引：70

作者：

Bai, Zengbing ^{[1
]}

Cai, Chuangxu ^{[1
]}

Sheng, Wangjian ^{[1
]}

Ren, Yuxiang ^{[1
]}

Wang, Huan ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Adv Organ Mat, State Key Lab Coordinat,Chem Chem & Biomed Innova, 163 Xianlin Ave, Nanjing 210093, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2020年 / 59卷 / 34期

关键词：

C-H activation; cyclic peptides; macrocyclization; palladium catalysis; stapled peptide; ALPHA-AMINO-ACIDS; STEREOSELECTIVE-SYNTHESIS; ACTIVATION; FUNCTIONALIZATION; CYCLIZATION; C(SP(2))-H; STRATEGIES; BONDS;

D O I：

10.1002/anie.202007226

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Transition-metal-catalyzed C-H activation has shown potential in the functionalization of peptides with expanded structural diversity. Herein, the development of late-stage peptide macrocyclization methods by palladium-catalyzed site-selective C(sp(2))-H olefination of tryptophan residues at the C2 and C4 positions is reported. This strategy utilizes the peptide backbone as endogenous directing groups and provides access to peptide macrocycles with unique Trp-alkene crosslinks.

引用

页码：14686 / 14692

页数：7

共 50 条

[1] Backbone-Enabled Directional Peptide Macrocyclization through Late-Stage Palladium-Catalyzed δ-C(sp2)-H Olefination
Bai, Zengbing
Cai, Chuangxu
Yu, Zonglun
Wang, Huan
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (42) : 13912 - 13916
[2] Backbone-Enabled Peptide Macrocyclization through Late-Stage Palladium-Catalyzed C-H Activation
Bai, Zengbing
Wang, Huan
SYNLETT, 2020, 31 (03) : 199 - 204
[3] Late-Stage Macrocyclization of Bioactive Peptides with Internal Oxazole Motifs via Palladium-Catalyzed C-H Olefination
Liu, Shu
Cai, Chuangxu
Bai, Zengbing
Sheng, Wangjian
Tan, Jiantao
Wang, Huan
ORGANIC LETTERS, 2021, 23 (08) : 2933 - 2937
[4] Macrocyclization of peptidoarylacetamides with self-assembly properties through late-stage palladium-catalyzed C(sp2)-H olefination
Tan, Jiantao
Wu, Jie
Liu, Shu
Yao, Hequan
Wang, Huan
SCIENCE ADVANCES, 2019, 5 (03)
[5] Palladium(ii) catalyzed site-selective C-H olefination of imidazo[1,2-a]pyridines
Tali, Javeed Ahmad
Kumar, Gulshan
Singh, Davinder
Shankar, Ravi
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (43) : 9401 - 9406
[6] Palladium-Catalyzed Site-Selective Fluorination of Unactivated C(sp3)-H Bonds
Miao, Jinmin
Yang, Ke
Kurek, Martin
Ge, Haibo
ORGANIC LETTERS, 2015, 17 (15) : 3738 - 3741
[7] Palladium-Catalyzed C-2 Selective C-H Olefination of Pyridines
Wen, Ping
Li, Yanmei
Zhou, Kang
Ma, Chao
Lan, Xiaobo
Ma, Chaowei
Huang, Guosheng
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) : 2135 - 2140
[8] Macrocyclization of bioactive peptides with internal thiazole motifs via palladium-catalyzed C-H olefination
Cai, Chuangxu
Wang, Feifei
Xiao, Xiuyun
Sheng, Wangjian
Liu, Shu
Chen, Jun
Zheng, Jie
Xie, Ran
Bai, Zengbing
Wang, Huan
CHEMICAL COMMUNICATIONS, 2022, 58 (31) : 4861 - 4864
[9] Late-Stage Peptide Diversification by Position-Selective C-H Activation
Wang, Wei
Lorion, Melanie M.
Shah, Jagrut
Kapdi, Anant R.
Ackermann, Lutz
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (45) : 14700 - 14717
[10] Peptide-guided functionalization and macrocyclization of bioactive peptidosulfonamides by Pd(II)-catalyzed late-stage C-H activation
Tang, Jian
Chen, Hongfei
He, Yadong
Sheng, Wangjian
Bai, Qingqing
Wang, Huan
NATURE COMMUNICATIONS, 2018, 9

← 1 2 3 4 5 →