Biological glycosidation of macrolide aglycones. II. Isolation and characterization of desosaminyl-platenolide I.
Biological glycosidation of platenolide I (I), a biosynthetic intermediate of 16-membered macrolide antibiotic platenomycin aglycones, with desosamine by Streptomycetes producing 14-membered macrolide antibiotics was attempted. Streptomyces narbonensis producing narbomycin gave a new product designated as 5-O-desosaminyl-platenolide I (III), and Streptomyces venezuelae producing narbomycin and picromycin gave III together with a second new product, 5-O-desosaminyl-14-hydroxyplatenolide I (IV). A nonantibiotic-producing blocked mutant of Streptomyces platensis subsp. malvinus, a producer of platenomycins, converted III to an antibiotically active compound identified as 3-O-propionyl-5-O-desosaminyl-9-dihydro-18-oxo-platenolide I (V).
D000617:Aminoglycosides / Q000096:biosynthesis; D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000302:isolation & purification*; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005285:Fermentation; D018942:Macrolides; D013302:Streptomyces / Q000378:metabolism
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D018942:Macrolides; C016675:platenolide I