Late‐Stage Peptide Macrocyclization by Palladium‐Catalyzed Site‐Selective C−H Olefination of Tryptophan
Zengbing Bai, Chuangxu Cai, Wangjian Sheng, Yuxiang Ren, Huan Wang
Abstract
Abstract Transition‐metal‐catalyzed C−H activation has shown potential in the functionalization of peptides with expanded structural diversity. Herein, the development of late‐stage peptide macrocyclization methods by palladium‐catalyzed site‐selective C(sp 2 )−H olefination of tryptophan residues at the C2 and C4 positions is reported. This strategy utilizes the peptide backbone as endogenous directing groups and provides access to peptide macrocycles with unique Trp–alkene crosslinks.
Topics & Concepts
ChemistryPeptideAlkenePalladiumTryptophanCatalysisStereochemistryCombinatorial chemistryOrganic chemistryBiochemistryAmino acidChemical Synthesis and AnalysisCatalytic C–H Functionalization MethodsClick Chemistry and Applications