Construction of Peptide Macrocycles via Palladium-Catalyzed Multiple S-Arylation: An Effective Strategy to Expand the Structural Diversity of Cross-Linkers
Xin Chu, Linhua Shen, Bo Li, Peng Yang, Cheng‐Zhuo Du, Xiaoye Wang, Gang He, Samir Messaoudi, Gong Chen
Abstract
A simple and versatile method for macrocyclizing unprotected native peptides with a wide range of easily accessible diiodo and triiodoarene reagents via the palladium-catalyzed multiple S-arylation of cysteine residues is developed. Iodoarenes with different arene and heteroarene cores can be incorporated into peptide macrocycles of varied ring sizes and amino acid compositions with high efficiency and selectivity under mild conditions.
Topics & Concepts
ChemistryPalladiumCombinatorial chemistryCatalysisPeptideReagentSelectivityCysteineRing (chemistry)Amino acidStereochemistryOrganic chemistryBiochemistryEnzymeChemical Synthesis and AnalysisSulfur-Based Synthesis TechniquesClick Chemistry and Applications