6‘-Deamino-6’-hydroxy derivatives, as intermediates in the biosynthesis of neomycin and paromomycin

Abstract

From broths of a neomycin producing Streptomices 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. © 1981, JAPAN ANTIBIOTICS RESEARCH ASSOCIATION. All rights reserved.