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The myriad of surface glycoconjugates in both the bacterial cell envelope and our gut cells dominate the microbiota\u2010host interface and play a critical role in host response and microbiota homeostasis. Among these, peptidoglycan is the basic glycan polymer offering the cell rigidity and a basis on which many other glycoconjugates are anchored. To directly study peptidoglycan in gut commensals and obtain the molecular insight required to understand their functional activities we need effective techniques like chemical probes to label peptidoglycan in live bacteria. Here we report a chemically guided approach to study peptidoglycan in a key mucin\u2010degrading gut microbiota member of the <jats:italic>Verrucomicrobia<\/jats:italic> phylum, <jats:italic>Akkermansia muciniphila<\/jats:italic>. Two novel non\u2010toxic tetrazine click\u2010compatible peptidoglycan probes with either a cyclopropene or isonitrile handle allowed for the detection and imaging of peptidoglycan synthesis in this intestinal species.<\/jats:p>","DOI":"10.1002\/cbic.202400037","type":"journal-article","created":{"date-parts":[[2024,4,30]],"date-time":"2024-04-30T22:21:14Z","timestamp":1714515674000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Probing Peptidoglycan Synthesis in the Gut Commensal <i>Akkermansia Muciniphila<\/i> with Bioorthogonal Chemical Reporters"],"prefix":"10.1002","volume":"25","author":[{"given":"Tjerk J.","family":"Sminia","sequence":"first","affiliation":[{"name":"Laboratory of Organic Chemistry Wageningen University and Research  Wageningen, The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Steven","family":"Aalvink","sequence":"additional","affiliation":[{"name":"Laboratory of Microbiology Wageningen University and Research  Wageningen, The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hanna","family":"de Jong","sequence":"additional","affiliation":[{"name":"Department of Chemical Biology and Drug Discovery Utrecht Institute for Pharmaceutical Sciences and Bijvoet Center for Biomolecular Research Utrecht University  Utrecht, The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marcel H.","family":"Tempelaars","sequence":"additional","affiliation":[{"name":"Laboratory of Food Microbiology Wageningen University and Research  Wageningen, The Netherlands"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5773-8506","authenticated-orcid":false,"given":"Han","family":"Zuilhof","sequence":"additional","affiliation":[{"name":"Laboratory of Organic Chemistry Wageningen University and Research  Wageningen, The Netherlands"},{"name":"School of Pharmaceutical Science and Technology Tianjin University  Tianjin P.R. 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