The biosynthesis of streptomycin. Incorporation of 14C-labelled compounds into streptose and N-methyl-l-glucosamine

Abstract

Although the structure of streptomycin has been known for some time, the process of its biosynthesis by Streptomyce8 gri8eua has not yet been elucidated. Blumsom & Baddiley (1961) examined extracts of S. gri8eU8 for nucleotide-sugar compounds which may be involved in synthesis of the streptose and N-methyl-L-glucosamine moieties of streptomycin. They found thymidine diphosphate rhamnose a possible intermediate for streptose, but no compounds more closely related to streptomycin were identified. Other workers have grown S. gri8eu8 in the presence of labelled compounds and examined the incorporation of the isotope into the streptomycin produced. Such experiments were first carried out by Karow, Peck, Rosenblum & Wood

Analysis of impurities in streptomycin and dihydrostreptomycin by hydrophilic interaction chromatography/electrospray ionization quadrupole ion trap/time‐of‐flight mass spectrometry

“…As the source of the methyl group of the N-methyl-L- glucosamine moiety is L-methionine, 30 the N,N-dimethyl group (not the N-ethyl group) would be appropriate for compound 18. Mannosidostreptomycin (compound 19) was also detected.…”

3-O-methyl-d-mannose from Streptomyces griseus

“…Growth of organism. Streptomyces griseu8 (Glaxo strain L118) was grown on slopes as described by Candy et al (1964). The resulting spores were used to inoculate 100ml.…”

Biosynthesis and Mutasynthesis of Aminoglycoside Antibiotics

“…They suggested that this reaction proceeded via two carbonyl intermediates, dTDP-6-deoxY-L-arabino-4-hexulose (16) and dTDP-6-deoxY-L-arabino-3-hexulose (17), and further assumed that dTDP-streptose (19) might be formed by a single rearrangement of either one of these two carbonyl intermediates. Subsequently, they (CANDY et al 1964;CANDY and BADDILEY 1965) demonstrated that C-l, C-3, and C-6 of glucose corresponded to C-l, C-3a (the formyl carbon), and C-6 (the methyl carbon), respectively, and assumed that the 4-hexulose (16) might be an intermediate from Dglucose. The above assumption was supported by HORNER (1966, 1969) who showed that C-2 of streptose arose from C-2 of glucose.…”