Volume 31 (1978) Issue 1 Pages 74-81
The preparation of the deoxy-analogues of two pseudodisaccharide fragments of neomycin, 5-O-β-D-ribofuranosyl-2, 6-dideoxy-streptamine and 6-deoxyneamine is described. When added to the growth medium of a deoxystreptamine-idiotroph of Streptomyces rimosus forma paromomycinus only the latter was incorporated into antibiotic, suggesting in obligatory order for the assembly of sub-units. 4-O-β-D-Ribofuranosyl-2, 6-dideoxystreptamine was also prepared. When added to the growth medium of a deoxystreptamine-idiotroph of Streptomyces fradiae it was converted into the 6-deoxyneomycins, apparently after hydrolysis to 2, 6-dideoxystreptamine. The structure of the protected derivatives of the ribofuranosyl 2, 6-dideoxystreptamines, potentially useful intermediates for the synthesis of novel antibiotics, was shown by using 13C NMR spectroscopy.