Mannosidostreptomycin

Streptomycin B (mannosidostreptomycin) has a mannose molecule attached to the methylglucosamine group, and is the first antibacterial product made, but is enzymatically converted to streptomycin later in the fermentation. 

The separation of aminodeoxy sugars from neutral and acidic sugars may be readily achieved using an acetate buffer at pH 5 (the iV-acetyl derivatives of D-glucosamine and n-galactosamine have characteristic Mg values in borate buffer at pH 10). M. C. Foster and Ashton have found zone electrophoresis to be useful in the separation of streptomycin components. They observed the following mobilities X 10 ) streptomycin, 22.5 mannosidostreptomycin, 19.5 streptothricin, 24.0 streptidine, 24.9 and streptamine, 6.3. 

During the elucidation of the structure of mannosidostreptomycin by methylation. Fried and Stavely isolated two derivatives of a dimethyl ether of iV-methyl-L-glucosamine. In order to compare their physical constants with those of a known compound in the n-series. Fried and Walz prepared derivatives of 2-deoxy-3,6-di-0-methyl-2-methylamino-n-glucose. The addition of methylamine and hydrogen cyanide to 2,5-di-0-methyl-D-arabinose (prepared by the periodate oxidation of 3,6-di-O-methyl-D-glucose) was followed by hydrolysis, and jdelded a mixture of a dextro- and a levo-rotatory acid. The dextrorotatory product was con-... 

Inamine E, Demain AL Mannosidostreptomycin hydrolase. Meth Enzymol 1975 43 637-640. Cundliffe E. Glycosylation of macrolide antibiotics in extracts of Screptomyces Itcidans. Antimicrob Agents Chcmoihcr 1992 36 348-352. 

Mannosidostreptomycin, a biologically active analog, according to a recent report. is not adenylated by a kinase capable of inactivating streptomycin. Intriguingly. adenosine, as well as the C-nucleoside formy-cin is a competitive inhibitor of ATP which serves as phosphate donor in the inactivation of kanamycin by a phosphorylase of aeruginosa. ... 

In addition to the above modifications of the streptomycin structure there exists a fourth compound, mannosidostreptomycin (streptomycin B), this compound is an a mannoside of streptomycin (Fig. 4). 

It is of interest that a mutant strain of S. griseus has been isolated which produces httle mannosidostreptomycin (5 % of total). This mutant strain was derived from an initial strain which produced up to 45% of the total streptomycin as mannosidostreptomycin (Alikhanian, 1962). Such evidence favors pathway A rather than B. 

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