Labeling and Characterization of Phenol-Containing Glycopeptides Using Chemoselective Probes with Isotope Tags.
Tsung-Shing Andrew WangRuo-Yu WuYu HongZhe-Chong WangTsung-Lin LiJiun-Jie ShieCheng-Chih HsuPublished in: Chembiochem : a European journal of chemical biology (2021)
Secondary metabolites are structurally diverse natural products (NPs) and have been widely used for medical applications. Developing new tools to enrich NPs can be a promising solution to isolate novel NPs from the native and complex samples. Here, we developed native and deuterated chemoselective labeling probes to target phenol-containing glycopeptides by the ene-type labeling used in proteomic research. The clickable azido-linker was included for further biotin functionalization to facilitate the enrichment of labeled substrates. Afterward, our chemoselective method, in conjunction with LC-MS and MSn analysis, was demonstrated in bacterial cultures. A vancomycin-related phenol-containing glycopeptide was labeled and characterized by our labeling strategy, showing its potential in glycopeptide discovery in complex environments.