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Facing the risks of serious antibiotic resistance and even the collapse of last\u2010line defenses, we designed and synthesized 40 novel norvancomycin derivatives to combat the threat. 32 compounds are single N\u2010terminally modified derivatives generated through simple and efficient methods. Diversity at the N\u2010terminus was greatly enriched, mainly by lipophilic attachment and strategies for the introduction of lipo\u2010sulfonium moieties for extensive structure\u2013activity relationship analysis. The first incorporation of a sulfonium moiety into the norvancomycin structure gave rise to compounds that exhibited 4\u2010 to 2048\u2010fold higher activity against vancomycin\u2010resistant bacteria VISA and VRE. This N\u2010terminal modification for norvancomycin provides an alternatively useful and promising strategy to restore the antibacterial activity of glycopeptide antibiotics against resistant bacteria, highlighting the same importance of the N\u2010terminal site as well as the vancosamine position, which is worth further study and development.<\/jats:p>","DOI":"10.1002\/cmdc.202200708","type":"journal-article","created":{"date-parts":[[2023,2,23]],"date-time":"2023-02-23T21:59:20Z","timestamp":1677189560000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Single Modification at the N\u2010Terminus of Norvancomycin to Combat Drug\u2010Resistant Gram\u2010Positive Bacteria"],"prefix":"10.1002","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-7814-1116","authenticated-orcid":false,"given":"Dongliang","family":"Guan","sequence":"first","affiliation":[{"name":"CAS Key Laboratory of Receptor Research CAS Center for Excellence in Molecular Cell Science Shanghai Institute of Materia Medica Chinese Academy of Sciences  555 Zuchongzhi Road, Pudong Shanghai 201203 P. 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