6"'-Deamino-6"'-hydroxy derivatives, as intermediates in the biosynthesis of neomycin and paromomycin.
From broths of a neomycin producing Streptomyces fradiae and of a mutant of Streptomyces rimosus forma paromomycinus respectively, 6"'-deamino-6"'-hydroxyneomycin and 6"'-deamino-6"'hydroxyparomomycin were obtained and their structures established by mass and 13C-NMR spectroscopy and by the study of hydrolytic fragments. These new compounds, which are both present as two epimers at C-5"', are suggested as intermediates in the biosynthesis of the parent antibiotics. The place and the mechanism of the 5"'-epimerisation and of the 6"'-amination are discussed.
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005285:Fermentation; D006868:Hydrolysis; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D009154:Mutation; D009355:Neomycin / Q000096:biosynthesis*; D010303:Paromomycin / Q000096:biosynthesis*; D013302:Streptomyces / Q000378:metabolism*
D010303:Paromomycin; D009355:Neomycin