4-N-acylfortimicins B and the preparation of fortimicin A from fortimicin B.
Selective 4-N-acylation of fortimicin B (2) has been accomplished by 4-N-acylation of 1,2',6'-tri-N-benzyloxycarbonylfortimicin B (4) followed by hydrogenolysis of the N-protecting benzyloxycarbonyl groups. In this manner, fortimicin B was converted into fortimicin A (1), and a series of 4-N-acylfortimicins B (3) was prepared for antibacterial assay. The key intermediate, 1,2',6'-tri-N-benzyloxycarbonylfortimicin B, was prepared either directly from fortimicin B or by converting fortimicin A into 1,2',6',2''-tetra-N-benzyloxycarbonylfortimicin A (6a), followed by selective hydrolysis of the 4-N-(N-benzyloxycarbonyl)glycyl group of the latter.
D000215:Acylation; D000617:Aminoglycosides / Q000138:chemical synthesis / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; C023385:fortimicin B; C023384:fortimicin A