Ynamide-Mediated Thioester Synthesis
Xuewei Wang, Yongli Zhao, Jinhua Yang, LI Yan-xi, Ying Luo, Mengyao Xu, Junfeng Zhao
Abstract
A novel ynamide-mediated thioester synthesis strategy was developed. Importantly, no detectable racemization was observed for the thioesterifications of carboxylic acids containing an α-chiral center, enabling it to be useful for the synthesis of peptide thioester, which is the key component of native chemical ligation. It is worth mentioning that amino acid side chain functional groups such as -OH and indole -NH are compatible with the reaction conditions, rendering their protection unnecessary. Moreover, this method was also amenable to selenoesters.
Topics & Concepts
ThioesterRacemizationChemistryNative chemical ligationCombinatorial chemistryPeptide synthesisPeptideStereochemistryOrganic chemistryBiochemistryCysteineEnzymeChemical Synthesis and AnalysisSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions