Biological glycosidation of macrolide aglycones. II. Isolation and characterization of desosaminyl-platenolide I.

Abstract
Biological glycosidation of platernolide I, a biosynthetic intermediate of 16-membered macrolide antibiotic platenomycin aglycones, with desosamine by Streptomyces producing 14-membered macrolide antibiotics was attempted. S. narbonensis, producing narbomycin, gave a new product designated as 5-O-desosaminyl-platenolide I (III), and S. venezuelae, producing narbomycin and picromycin, gave III and a 2nd new product, 5-O-desosaminyl-14-hydroxyplatenolide I. A nonantibiotic-producing blocked mutant of S. platensis ssp. 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.