Traceless Peptide and Protein Modification via Rational Tuning of Pyridiniums
Chuan Wan, Yichi Zhang, Jinpeng Wang, Yun Xing, Dongyan Yang, Qinhong Luo, Jianbo Liu, Yuxin Ye, Zhihong Liu, Feng Yin, Rui Wang, Zigang Li
Abstract
Herein, we report a versatile reaction platform for tracelessly cleavable cysteine-selective peptide/protein modification. This platform offers highly tunable and predictable conjugation and cleavage by rationally estimating the electron effect on the nucleophilic halopyridiniums. Cleavable peptide stapling, antibody conjugation, enzyme masking/de-masking, and proteome labeling were achieved based on this facile pyridinium-thiol-exchange protocol.
Topics & Concepts
ChemistryPeptidePyridiniumCombinatorial chemistryCysteineNucleophileCleavage (geology)Masking (illustration)ThiolProteomeBioconjugationPosttranslational modificationEnzymeBiochemistryOrganic chemistryCatalysisArtGeotechnical engineeringVisual artsEngineeringFracture (geology)Click Chemistry and ApplicationsChemical Synthesis and AnalysisPeptidase Inhibition and Analysis