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

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