Demethylative Alkylation of Methionine Residue by Employing the Sulfonium as the Key Intermediate
Qi-Long Hu, Jia-Tian Liu, Jian Li, Ge Yang, Zhendong Song, Albert S. C. Chan, Xiao‐Feng Xiong
Abstract
Methionine (Met) offers a valuable handle to achieve peptide chemical modification owing to its unique thioether functional group. In contrast with cysteine, the site-selective functionalization of the hydrophobic and redox-sensitive thioether motif on peptides is still challenging, and strategies for diversification on the Met residue are rarely disclosed. Herein we report a transition-metal-free and redox-neutral approach for Met diversification with substrate diversity, which could be applied to synthesize cyclic peptides.
Topics & Concepts
ChemistryThioetherSulfoniumCysteineAlkylationMethionineResidue (chemistry)Combinatorial chemistryPeptideRedoxMethionine sulfoxideStereochemistryOrganic chemistryBiochemistryEnzymeAmino acidCatalysisSalt (chemistry)Chemical Synthesis and AnalysisClick Chemistry and ApplicationsAntimicrobial Peptides and Activities