title: CuAAC-mediated diversification of aminoglycoside-arginine conjugate mimics by non-reducing di- and trisaccharides.
abstract: Di- and triguanidinylation of trehalose, sucrose, and melizitose has been achieved via a Huisgen-cycloaddition approach. They can serve as aminoglycoside-arginine conjugate mimics, which has been demonstrated by their biological profiles in assays against Bacillus subtilis. For comparative studies, tetraguanidinylated neamine and kanamycin derivatives have also been synthesized and evaluated.
authors.affiliation: Leibniz-Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, 06120 Halle, Germany. bwesterm@ipb-halle.de
authors.forename: Bernhard
authors.initials: B
authors.lastname: Westermann
authors.forename: Simon
authors.initials: S
authors.lastname: Dörner
authors.forename: Sebastian
authors.initials: S
authors.lastname: Brauch
authors.forename: Angela
authors.initials: A
authors.lastname: Schaks
authors.forename: Ramona
authors.initials: R
authors.lastname: Heinke
authors.forename: Sebastian
authors.initials: S
authors.lastname: Stark
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft
authors.forename: Sander S
authors.initials: SS
authors.lastname: van Berkel
mesh_terms: D000617:Aminoglycosides / Q000737:chemistry / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001120:Arginine / Q000737:chemistry / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects / Q000254:growth & development; D002236:Carbohydrate Conformation; D002384:Catalysis; D057930:Click Chemistry; D005601:Framycetin / Q000138:chemical synthesis / Q000494:pharmacology; D006001:Glycoconjugates / Q000737:chemistry / Q000494:pharmacology; D006146:Guanidines / Q000737:chemistry; D007612:Kanamycin / Q000138:chemical synthesis / Q000494:pharmacology; D062105:Molecular Docking Simulation; D018716:Molecular Mimicry; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D006001:Glycoconjugates; D006146:Guanidines; D014312:Trisaccharides; D005601:Framycetin; D013395:Sucrose; D007612:Kanamycin; C488396:neamine; D001120:Arginine; D014199:Trehalose