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

ISAO MAEZAWA, AKIO KINUMAKI, MAKOTO SUZUKI
1978 Journal of antibiotics (Tokyo. 1968)  
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 5-0-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).
more » ... 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-Odesosaminyl-9-dihydro-18-oxo-platenolide I (V). In the previous papers dealing with biosynthesis of narbomycin", picromycin" and platenomycins", the authors demonstrated that some macrolide aglycones were key substances for the elucidation of biosynthetic pathways of these antibiotics. By adding narbonolide, a 14-membered macrolide aglycone, in the fermentation medium of Streptomyces platensis subsp. malvinus, a producer of the 16membered macrolide antibiotic platenomycins, the authors also succeeded in producing some new narbonolide derivatives possessing mycaminose which generally combined to 16-membered macrolide antibiotics". Recently, LEMAHIEU et al. reported the production of 3-O-oleandrosyl-5-O-desosaminyl-erythronolide A oxime by the oleandomycin-producing strain'). These findings show that an aglycone of a macrolide antibiotic is useful not only for the biogenetic studies, but also as a starting material for developing new macrolide antibiotics. The present paper deals with the glycosidation of platenolide I (I)"), a biosynthetic intermediate of 16-membered macrolide antibiotic platenomycin aglycones, with desosamine by S. narbonensis ISP 5016 and S. venezuelae MCRL 0376, resulting in the production of 5-0-desosaminylplatenolide I (III) and/or 5-O-desosaminyl-14-hydroxy-platenolide I (IV). The result suggests that the glycosidation of a macrolide aglycone with a foreign aminosugar is achieved by an appropriate macrolide antibiotic-producing strain. The paper also deals with the biological conversion of the non-antibiotic substance, III to an antibiotically active 3-O-propionyl-5-O-desosaminyl-9-dihydro-l8oxo-platenolide I (V) by a blocked mutant of S. platensis subsp. malvinus. Materials and Methods Microorganisms and Culture Conditions Streptomyces narbonensis ISP 5016, a producer of narbomycin, and Streptomyces venezuelae MCRL 0376, a producer of narbomycin and picromycin as major macrolide antibiotics, were used as desosamine donors. A blocked mutant U 211) of platenomycin-producing Streptomyces platensis subsp.
doi:10.7164/antibiotics.31.309 fatcat:724v3anznjbfpklxzfhnjjhb2i