Journal of the Chemical Society. Perkin transactions I p. 2283 - 2286 (1988)
Update date:2022-08-05
Topics:
Palaniswamy, Venkatapuram A.
Gould, Steven J.
Aspects of the biosynthesis of the D-gulosamine moiety of the antibiotic streptothricin F have been studied with stable isotopes.After having obtained substantial incorporation (ca. 9 percent) of <1-(14)C>-D-glucosamine into the total compound, <2-(13)C, (15)N>-D-glucosamine was synthesized and fed to Streptomyces L-1689-23.Analysis of the (13)C n.m.r. spectrum of the derived antibiotic reveals a doublet (JCN 11.4 Hz) for the C-8 resonance (3.1 percent enrichment in both (13)C and (15)N), indicating the intact incorporation of the material fed and establishing D-glucosamine as a direct precursor to streptothricin. <1-(2)H>-D-Glucose has been synthesized and incorporated into streptothricin with retention of the deuterium label at 7-H (1.8 percent enrichment) and incorporation of deuterium at 17-H/18-H (0.4 percent enrichment); data from the incorporation of <1-(14)C>-D-glucose that had been CO-fed indicate extensive metabolism into other parts of the structure.Incorporation of <2-(2)H>-D-glucose leads only to deuterium enrichment at 17-H/18-H (0.09 percent enrichment), indicating that 2-H is apparently lost in the phosphoglucose isomerase reaction of this organism.
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