Synthesis of (+),(-)-neamine and their positional isomers as potential antibiotics.
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.
Ryu
Do Hyun
DH
Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 45 Shattuck Street, Boston, MA 02115, USA.
Tan
Choon-Hong
CH
Rando
Robert R
RR
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*
D000900:Anti-Bacterial Agents; D012335:RNA, Ribosomal; D009355:Neomycin