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Biosynthesis of Streptomycin

III. ORIGIN OF THE CARBON ATOMS OF STREPTOSE

Joseph Bruton 1 and William H. Horner 1

From the 1 From the Department of Biochemistry, Schools of Medicine and Dentistry, Georgetown University, Washington D. C. 20007

The pathway of synthesis by Streptomyces griseus of the streptose moiety of streptomycin from D-glucose has been studied. L-Serine-3-14C, D-glucose-l-14C, D-glucose-2-14C, D-glucose-3,4-14C, and D-glucose-6-14C were given to streptomycin-producing cultures. A 40 to 46% incorporation of 14C into the streptose moiety of the isolated streptomycin was found. Procedures for the total degradation of streptose were developed and utilized to determine the 14C-label pattern in this moiety. Examination of the isotope distribution data for the 6 carbons of streptose after administration of the above labeled compounds to the organism shows that streptose arises from a carbon-carbon rearrangement at carbon atoms 3 and 4 of glucose to form the branched sugar, streptose.

Submitted on November 26, 1966


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