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

文献类型：期刊论文

作者Hu, Shulei3,4; Zhang, Yu2,3; Xie, Xiong3; Li, Luhan1,3; Chen, Kaixian3,4; Liu, Hong1,3,4; Wang, Jiang2,3
刊名CHINESE CHEMICAL LETTERS
出版日期2024-08-01
卷号35期号:8页码:8
关键词C -H functionalization Rh(III)-catalyzed Alkenylation Cyclic peptides Macrolactamization
ISSN号1001-8417
DOI10.1016/j.cclet.2023.109408
通讯作者Chen, Kaixian(kxchen@simm.ac.cn) ; Liu, Hong(hliu@simm.ac.cn) ; Wang, Jiang(jwang@lglab.ac.cn)
英文摘要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.
WOS关键词ACCESS
资助项目National Key R&D Program of China[2022YFA1302900] ; National Natural Science Foundation of China[82130105] ; National Natural Science Foundation of China[22337003] ; National Natural Science Foundation of China[82121005] ; National Natural Science Foundation of China[22177124] ; National Natural Science Foundation of China[82322063] ; Program of Shanghai Academic Research Leader[23XD1460300] ; Lingang Laboratory[LG-GG-202204-02]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001325475800001
出版者ELSEVIER SCIENCE INC
源URL[http://119.78.100.183/handle/2S10ELR8/313615]  
专题新药研究国家重点实验室
通讯作者Chen, Kaixian; Liu, Hong; Wang, Jiang
作者单位1.ShanghaiTech Univ, Sch Life Sci & Technol, Shanghai 200031, Peoples R China
2.Lingang Lab, Shanghai 200031, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
4.China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 211198, Peoples R China
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):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),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):8.

入库方式： OAI收割

来源：上海药物研究所

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