Rhodium(III)-Catalyzed C–H Alkenylation: Access to Maleimide-Decorated Tryptophan and Tryptophan-Containing Peptides
Jingjing Peng, Chunpu Li, Mirzadavlat Khamrakulov, Jiang Wang, Hong Liu
Abstract
Maleimide is widely applied in many fields, especially in antibody-drug conjugations and peptide drugs. Herein, we develop a strategy for the C-H alkenylation of tryptophan and tryptophan-containing peptides, providing a synthetic route of decorating maleimide on peptides. The method has a high tolerance of functional groups and protecting groups. Furthermore, this method was applied to prepare peptide conjugation with molecules such as drugs and fluorescence probes. Moreover, macrocyclic peptides were obtained via this reaction.
Topics & Concepts
MaleimideChemistryTryptophanRhodiumCatalysisCombinatorial chemistryPolymer chemistryOrganic chemistryBiochemistryAmino acidCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms