Copper(I)-Catalyzed Late-Stage Introduction of Oxime Ethers into Peptides at the Carboxylic Acid Site

We have developed a method of introducing biological oxime ether fragments into peptides by CuI-catalyzed late-stage modification and functionalization of peptides, utilizing their acid moiety and varied 2H-azirines. As a result of its mild conditions, high atom economy, moderate yield, and excellen...

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Bibliographic Details
Published in:Organic letters 2022-12, Vol.24 (50), p.9248-9253
Main Authors: Liu, Yuyang, He, Zeyuan, Ma, Wen, Bao, Guangjun, Li, Yiping, Yu, Changjun, Li, Jingyue, E, Ruiyao, Xu, Zhaoqing, Wang, Rui, Sun, Wangsheng
Format: Article
Language:English
Subjects:
Carboxylic Acids
Catalysis
Copper
Ethers
Oximes
Peptides
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Summary:We have developed a method of introducing biological oxime ether fragments into peptides by CuI-catalyzed late-stage modification and functionalization of peptides, utilizing their acid moiety and varied 2H-azirines. As a result of its mild conditions, high atom economy, moderate yield, and excellent functional-group tolerance, the method can provide access to late-stage peptide modification and functionalization at their acid sites both in the homogeneous phase and on resins in SPPS, providing a new tool kit for peptide functionalization, diversification, and fluorescent labeling.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03813