[Synthesis of a disaccharide with antibiotic activity].
The aminodisaccharide glycoside methyl 2,4-diamino-2,4-dideoxy-6-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl)- beta-D-glucopyranoside (4), which exhibits a structural resemblance to neamine, was synthesized via the azido method. Starting from 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-alpha-D-glucopyranosyl bromide, the alpha-D-glycosylation of O-6 of methyl 2,4-diazido-3-O-benzyl-2,4-dideoxy-beta-D-glucopyranoside was accomplished stereoselectively at low temperatures in the presence of mercury bromide. Against some gram-negative test-organisms, the activity of 4 was found to be in the same range as neamine, but directed against different germs.
D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects; D007709:Klebsiella / Q000187:drug effects; D011549:Pseudomonas / Q000187:drug effects
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; C038428:methyl-2,4-diamino-2,4-dideoxy-6-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl)-beta-D-glucopyranoside
Synthese eines Antibiotisch Aktiven Disaccharids.