A Sulfonium Triggered Thiol-yne Reaction for Cysteine Modification
Zhanfeng Hou, Dongyuan Wang, Yang Li, Rongtong Zhao, Chuan Wan, Yue Ma, Chenshan Lian, Feng Yin, Zigang Li
Abstract
We report a facile thiol-yne type reaction triggered by the sulfonium center. After facile propargylation of thiolethers, the resulting sulfonium could undergo facile addition with thiols in aqueous media at ambient temperature. Further applying this reaction in unprotected peptides bearing neighboring methionine and cysteine could enable a facile intramolecular addition to construct cyclic peptides with better stability, good glutathione resistance, and increased cellular uptakes. Also, the propargylated sulfonium may be used as robust and versatile probes to target cysteines containing biomolecules.
Topics & Concepts
SulfoniumChemistryCysteineThiolIntramolecular forceCombinatorial chemistryBiomoleculeMethionineGlutathioneAqueous solutionAqueous mediumOrganic chemistryAmino acidBiochemistryEnzymeSalt (chemistry)Click Chemistry and ApplicationsSulfur-Based Synthesis TechniquesChemical Synthesis and Analysis