Streptomycin, dihydro

Streptidine phosphate was incubated with dTDP-L-[U-14C]dihydro-streptose, obtained in situ from dTDP-D-[U-14C]glucose with a cell-free extract from S. griseus. Two new, positively charged, radioactive products were obtained which, upon hydrolysis, gave dihydrostreptose as the only radioactive product. Comparison with a synthetic sample of 0-a-L-dihydrostreptose-(l- 4)-streptidine (43, see Scheme 14) proved that one of the products was identical with this pseudodisaccharide, and the second product was identified as the corresponding 6-phosphate (44). It was concluded that the phospho-rylated product had been partially hydrolyzed during the incubation by streptomycin 6-phosphate phosphatase present in the cell-free extract. No transfer-products were formed in controls in which (a) denatured extract was used,(fe) streptidine phosphate was absent, or(c) streptidine was substituted for streptidine phosphate. 

Both methanolysis and mercaptolysis of streptomycin B yielded known derivatives of streptidine, streptobiosamine and D-mannose, while dihydrostreptomycin B yielded derivatives of streptidine, dihydro-streptobiosamine and D-mannose.The derivatives of D-mannose which were obtained are listed in Table II. These results, together with the analytical data for the hydrochloride and reineckate of streptomycin B, established the composition of the free base as C27H490nN7 and showed that the substance exists as glycosidically linked streptidine,... 

Stebbins WC, Moody DB, Hawkins JE Jr, Johnsson LG, Norat MA (1987) The species-specific nature of the ototoxicity of dihydro-streptomycin in the patas monkey. Neurotoxicology 8(l) 33-44... 

The method based on colour formation with diacetyl and a-naphthol in alkaline solution, described above for streptomycin, is equally applicable to the dihydro-compound. 

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