Rh(III)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks

doi:10.1016/j.cclet.2023.109408

	Rh(III)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks
	Hu, Shulei 1,2; Zhang, Yu 2,3; Xie, Xiong 2; Li, Luhan2,4 ; Chen, Kaixian 1,2; Liu, Hong1,2,4 ; Wang, Jiang 2,3
	2024-08-01
发表期刊	CHINESE CHEMICAL LETTERS (IF:9.4[JCR-2023],7.3[5-Year])
ISSN	1001-8417
EISSN	1878-5964
卷号	35 期号:8
发表状态	已发表
DOI	10.1016/j.cclet.2023.109408
摘要	Heterocycle-braced cyclic peptides have demonstrated enhanced metabolic stability, increased potency and selectivity. Here, we present a rapid synthesis method for constructing Trp(C7)-alkene(E)-crosslinked E )-crosslinked cyclic peptides with potent anti-proliferative activities against cancer cells, through C-H alkenylation and macrolactamization. This report addresses critical challenges associated with the installation and removal of the directing group N-Piv, configuration selectivity of the olefin, and intramolecular cyclization. Notably, this method exhibits mild reaction conditions, traceless removal of the directing group, and high configuration selectivity. (c) 2024 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
关键词	C -H functionalization Rh(III)-catalyzed Alkenylation Cyclic peptides Macrolactamization
URL	查看原文
收录类别	SCI
语种	英语
资助项目	National Key R&D Program of China[2022YFA1302900] ; National Natural Science Foundation of China[
WOS研究方向	Chemistry
WOS类目	Chemistry, Multidisciplinary
WOS记录号	WOS:001325475800001
出版者	ELSEVIER SCIENCE INC
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/433512
专题	生命科学与技术学院生命科学与技术学院_特聘教授组_柳红组生命科学与技术学院_硕士生
通讯作者	Chen, Kaixian; Liu, Hong; Wang, Jiang
作者单位	1.China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 211198, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 3.Lingang Lab, Shanghai 200031, Peoples R China 4.ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai 200031, Peoples R China
通讯作者单位	生命科学与技术学院
推荐引用方式 GB/T 7714	Hu, Shulei,Zhang, Yu,Xie, Xiong,et al. Rh(III)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks[J]. CHINESE CHEMICAL LETTERS,2024,35(8).
APA	Hu, Shulei.,Zhang, Yu.,Xie, Xiong.,Li, Luhan.,Chen, Kaixian.,...&Wang, Jiang.(2024).Rh(III)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks.CHINESE CHEMICAL LETTERS,35(8).
MLA	Hu, Shulei,et al."Rh(III)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks".CHINESE CHEMICAL LETTERS 35.8(2024).