Wang T.-S.AWu R.-YHong YWang Z.-CLi T.-LShie J.-JTSUNG-SHING WANGCHENG-CHIH HSU2021-08-032021-08-03202114394227https://www.scopus.com/inward/record.uri?eid=2-s2.0-85105485767&doi=10.1002%2fcbic.202100169&partnerID=40&md5=6eeed075c1702fa03d548cb72df71061https://scholars.lib.ntu.edu.tw/handle/123456789/575879Secondary 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. ? 2021 Wiley-VCH GmbH[SDGs]SDG3journal article10.1002/cbic.202100169339150222-s2.0-85105485767