Deoxy derivatives of butirosin A and 5"-amino-5"-deoxybutirosin A, aminoglycoside antibiotics resistant to bacterial 3'-phosphorylative enzymatic inactivation. Synthesis and NMR studies.
3'-Deoxybutirosin A (4), 5"-amino-3', 5"-dideoxybutirosin A (6), and 5"-amino-4', 5"-dideoxybutirosin A (7) were prepared by deoxygenation of the appropriate hydroxyl in suitably protected derivatives of butirosin A, using sequentially trifluoromethylsulfonylation, displacement with benzenethiolate, and hydrogenolysis. The structures of the compounds were confirmed by NMR spectroscopy, using 13C NMR and 1H NMR at up to 600 MHz. The compounds are broad-spectrum antibiotics active against resistant microorganisms which inactivate butirosin and related aminoglycosides by 3'-phosphorylation.
D000617:Aminoglycosides / Q000138:chemical synthesis; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D002076:Butirosin Sulfate / Q000138:chemical synthesis / Q000494:pharmacology / Q000031:analogs & derivatives; D004352:Drug Resistance, Microbial; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D010766:Phosphorylation
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D002076:Butirosin Sulfate; C035631:5''-amino-4',5''-dideoxybutirosin A; C035633:3'-deoxybutirosin A; C035632:5''-amino-3',5''-dideoxybutirosin A