Electrophilic Sulfonium-Promoted Peptide and Protein Amidation in Aqueous Media
Chuan Wan, Yuan Ping Feng, Zhanfeng Hou, Chenshan Lian, Liang Zhang, Yuhao An, Jinming Sun, Dongyan Yang, Chenran Jiang, Feng Yin, Rui Wang, Zigang Li
Abstract
A novel amidation strategy using electrophilic sulfonium, which is soluble and stable in aqueous conditions, was developed. The sulfoniums could activate thioacid and carboxyl acid to efficiently react with amines to afford amides. This method enables applications in amidation in both aqueous media and solid-phase peptide synthesis, peptide/protein modifications, and reactive lysines of a proteome at pH 10 with activity-based protein profiling. A peptide ligand-directed labeling of the USP7-UBL2 domain was also performed using this method.
Topics & Concepts
ChemistrySulfoniumElectrophilePeptideCombinatorial chemistryAqueous mediumAqueous solutionPeptide synthesisAmino acidOrganic chemistryBiochemistryCatalysisSalt (chemistry)Chemical Synthesis and AnalysisClick Chemistry and ApplicationsPeptidase Inhibition and Analysis