Semisynthetic aminoglycoside antibacterials. 6. Synthesis of sisomicin, Antibiotic G-52, and novel 6'-substituted analogues of sisomicin from aminoglycoside 66-40C.
The discovery of aminoglycoside 66-40C, a novel dimeric, unsaturated imine produced by Micromonospora inyoensis, afforded a versatile intermediate for the synthesis of a variety of sisomicin analogues modified at the 6' position. The conversion of 66-40C into sisomicin, antibiotic G-52, and a series of novel 6'-substituted analogues of sisomicin is described, and the biological activity of the products is discussed.
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000494:pharmacology / Q000633:toxicity; D001412:Bacillus subtilis / Q000187:drug effects; D004755:Enterobacteriaceae / Q000187:drug effects; D005839:Gentamicins / Q000138:chemical synthesis*; D007928:Lethal Dose 50; D051379:Mice; D008826:Microbial Sensitivity Tests; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D012853:Sisomicin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D013211:Staphylococcus aureus / Q000187:drug effects; D013297:Streptococcus pyogenes / Q000187:drug effects
D000617:Aminoglycosides; D000981:Antiprotozoal Agents; D005839:Gentamicins; C012632:6'-N-methylsisomicin; C015614:aminoglycoside 66-40C; D012853:Sisomicin