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Their aminolysis accommodates a broad range of nucleophiles, including complex bioactive amines, providing access to glycoconjugates that remain difficult to obtain by conventional methods. Beyond their synthetic utility, vic-HTCs display an unusual thiol reactivity in which exchange at a C(sp2) center and substitution at a remote C(sp3) site arise from a common tetrahedral intermediate. Combined experimental and DFT (Density Functional Theory) analyses show that chemoselectivity is governed by substituent-dependent kinetic partitioning rather than intrinsic hard-soft site differentiation, providing a mechanistic basis for describing vic-HTCs as pseudo-ambident electrophiles. Application of this platform to ciprofloxacin (Cip) afforded glycoconjugates without prior biological design. Two closely related conjugates differing only in the carbohydrate anomeric state exhibited sharply contrasting antibacterial profiles. The most active conjugate showed up to a 46-fold molar potency improvement over Cip against Staphylococcus aureus, while activity was retained or partially improved against Gram-negative strains, including Pseudomonas aeruginosa. These findings contrast with the commonly reported loss of activity upon fluoroquinolone glycoconjugation and demonstrate that carbohydrate architecture can enhance antibacterial potency.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01103","type":"journal-article","created":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T16:02:16Z","timestamp":1789228936000},"page":"12883-12901","source":"Crossref","is-referenced-by-count":0,"title":["Vicinal Halothiolcarbonates\nas Pseudo-Ambident Electrophiles:\nCarbamate Synthesis, Unified Thiol Reactivity, and Architecture-Dependent\nAntibacterial Activity of Ciprofloxacin Glycoconjugates"],"prefix":"10.1021","volume":"91","author":[{"given":"Siwar","family":"Mejri","sequence":"first","affiliation":[{"name":"Universite\u0301 de Picardie Jules Verne , , 10 Rue Baudelocque , ,","place":["Amiens Ce\u0301dex, France, 80039"]},{"name":"Universite\u0301 de Carthage , , ,","place":["Zarzouna-Bizerte, Tunisie, TN 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80039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas","family":"Dayez","sequence":"additional","affiliation":[{"name":"Universite\u0301 de Picardie Jules Verne , , 33 rue Saint Leu , ,","place":["Amiens cedex, France, 80039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohamed Amine","family":"Ben Maaouia","sequence":"additional","affiliation":[{"name":"Universite\u0301 de Picardie Jules Verne , , 10 Rue Baudelocque , ,","place":["Amiens Ce\u0301dex, France, 80039"]},{"name":"Universite\u0301 de Carthage , , ,","place":["Zarzouna-Bizerte, Tunisie, TN 7021"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Abed","family":"Bil","sequence":"additional","affiliation":[{"name":"Universite\u0301 de Picardie Jules Verne , , 10 Rue Baudelocque , ,","place":["Amiens Ce\u0301dex, France, 80039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Mathiron","sequence":"additional","affiliation":[{"name":"UFR des Sciences, Ba\u0302timent Serres-Transfert , Rue Dallery Passage du Sourire d\u2019Avril , ,","place":["Amiens Cedex 1, France, 80039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4927-3603","authenticated-orcid":true,"given":"Adam","family":"Duong","sequence":"additional","affiliation":[{"name":"Universite\u0301 de Picardie Jules Verne , , 10 Rue Baudelocque , ,","place":["Amiens Ce\u0301dex, France, 80039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christine","family":"Ce\u0301zard","sequence":"additional","affiliation":[{"name":"Universite\u0301 de Picardie Jules Verne , , 10 Rue Baudelocque , ,","place":["Amiens Ce\u0301dex, France, 80039"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rym","family":"Abidi","sequence":"additional","affiliation":[{"name":"Universite\u0301 de Carthage , , ,","place":["Zarzouna-Bizerte, Tunisie, TN 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