title: Synthesis of (+),(-)-neamine and their positional isomers as potential antibiotics.
abstract: The syntheses of (+)-neamine 1, (-)-neamine ent-1 and their positional isomers 2, 3, ent-2 and ent-3 are reported as potential new scaffolds for novel aminoglycoside antibiotics. These isomers exhibit similar inhibitory activities, as shown using an in vitro translation assay. A simple model is proposed to explain this lack of stereospecific binding to the ribosomal RNA.
authors.affiliation: Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 45 Shattuck Street, Boston, MA 02115, USA.
authors.forename: Do Hyun
authors.initials: DH
authors.lastname: Ryu
authors.forename: Choon-Hong
authors.initials: CH
authors.lastname: Tan
authors.forename: Robert R
authors.initials: RR
authors.lastname: Rando
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001665:Binding Sites; D007536:Isomerism; D009355:Neomycin / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014176:Protein Biosynthesis / Q000187:drug effects; D012335:RNA, Ribosomal / Q000037:antagonists & inhibitors / Q000378:metabolism*
chemical_list: D000900:Anti-Bacterial Agents; D012335:RNA, Ribosomal; D009355:Neomycin