6'''-DEAMINO-6'''-HYDROXY DERIVATIVES, AS INTERMEDIATES IN THE BIOSYNTHESIS OF NEOMYCIN AND PAROMOMYCIN

Abstract

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.