Copper(I)-Catalyzed Late-Stage Introduction of Oxime Ethers into Peptides at the Carboxylic Acid Site
Yuyang Liu, Zeyuan He, Wen Ma, Guangjun Bao, Yiping Li, Changjun Yu, Jingyue Li, E Ruiyao, Zhaoqing Xu, Rui Wang, Wangsheng Sun
Abstract
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.
Topics & Concepts
ChemistrySurface modificationMoietyOximeCatalysisCombinatorial chemistryPeptideCarboxylic acidEtherOrganic chemistryBiochemistryPhysical chemistryChemical Synthesis and AnalysisSynthesis and Catalytic ReactionsClick Chemistry and Applications