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Here, lipid\u2010carbohydrate\u2010peptidyl\u2010RNA conjugates were obtained by post\u2010functionalization reactions, solid\u2010phase synthesis, and enzymatic steps, to generate molecules mimicking the substrates of FmhB, an essential peptidoglycan synthesis enzyme of <jats:italic>Staphylococcus aureus<\/jats:italic>. Mimics of Gly\u2010tRNA<jats:sup>Gly<\/jats:sup> and lipid intermediate II (undecaprenyl\u2010diphospho\u2010disaccharide\u2010pentapeptide) were combined in a single \u201cbi\u2010substrate\u201d inhibitor (IC<jats:sub>50<\/jats:sub>=56\u2005n<jats:sc>m<\/jats:sc>). The synthetic route was exploited to generate substrates and inhibitors containing <jats:sc>d<\/jats:sc>\u2010lactate residue (<jats:sc>d<\/jats:sc>\u2010Lac) instead of <jats:sc>d<\/jats:sc>\u2010Ala at the C\u2010terminus of the pentapeptide stem, a modification responsible for vancomycin resistance in the enterococci. The substitution impaired recognition of peptidoglycan precursors by FmhB. The associated fitness cost may account for limited dissemination of vancomycin resistance genes in <jats:italic>S. aureus<\/jats:italic>.<\/jats:p>","DOI":"10.1002\/chem.201802360","type":"journal-article","created":{"date-parts":[[2018,7,19]],"date-time":"2018-07-19T02:53:45Z","timestamp":1531968825000},"page":"14911-14915","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Synthesis of Lipid\u2010Carbohydrate\u2010Peptidyl\u2010RNA Conjugates to Explore the Limits Imposed by the Substrate Specificity of Cell Wall Enzymes on the Acquisition of Drug Resistance"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8013-8311","authenticated-orcid":false,"given":"Matthieu","family":"Fonvielle","sequence":"first","affiliation":[{"name":"INSERM UMRS 1138, Sorbonne Universit\u00e9s, UPMC Univ Paris 06;, 'Sorbonne Paris Cit\u00e9, Universit\u00e9 Paris Descartes, Universit\u00e9 Paris Diderot 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