The Journal of Antibiotics
SUB-UNIT ASSEMBLY IN THE BIOSYNTHESIS OF NEOMYCIN
THE SYNTHESIS OF 5-O-β-D-RIBOFURANOSYL AND 4-O-β-D-RIBOFURANOSYL-2, 6-DIDEOXYSTREPTAMINES
CEDRIC J. PEARCEMUHAMMAD AKHTARJOHN E. G. BARNETTDANIEL MERCIERANNE-MARIE SEPULCHRESTEPHAN D. GERO
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Volume 31 (1978) Issue 1 Pages 74-81

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Abstract

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.

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