2-Deoxy-2-methylamino-L-glucose

Deoxy-2-methylamino-L-glucose (N-methyl-i.-glucosamine) NHCH, HO HO H HOH2 C—C—C—C—C—CHO H H HO H the antibiotic streptomycin... 

IV- methy 1-L- gluco s amine (2-deoxy-2-methylamino-L-glucose)... 

The other component parts of streptomycin, namely L-streptose and the aminosugar 2-deoxy-2-methylamino-L-glucose (A -methyl-L-glucosamine), are also ultimately derived from o-glucose. Gentamicin Ci contains two aminosugars, L-garosamine and D-purpurosamine. 

Whereas streptidine and 2-deoxy-2-(methylamino)-L-glucose, components of streptomycin, were synthesized by 1950, some fifteen years elapsed before the synthesis of streptose was achieved by Dyer and coworkers. Another synthesis of streptose was reported by Paulsen and coworkers. The glycosidic linkage between streptose and 2-deoxy-2-(methylamino)-L-glucose had previously been shown to be a-L, and the glycosidic linkage between streptose and streptidine has been revised to be o-L on the basis of n.m.r.-spectral studies. ... 

Deoxy-2-methylamino-D-gluconic acid, A-218 2-Deoxy-2-methylamino-D-glucose, A-266 2-Deoxy-2-methylamino-L-glucose, A-266... 

An unusual group of antibiotics, the aminoglycoside antibiotics, is based on oligosaccharide structures almost exclusively. Of particular therapeutic importance is streptomycin (an antituberculosis agent), isolated in 1944 from cultures of the mold Streptomyces griseus. The molecule consists of three subunits the furanose streptose, the glucose derivative 2-deoxy-2-methylamino-L-glucose (an example of the rare l form), and streptidine, which is actually a hexasubstituted cyclohexane. 

Such names as bacillosamine for 2,4-diamino-2,4,6-trideoxy-D-glucose and garosamine for 3-deoxy-4-C-methyl-3-methylamino-L-arabinose are not recommended, as they imply replacement of OH by NH2 in a nonexistent parent sugar. 

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-... 

While a 2-(D-arabino-tetritol-l-yl)-l-methylpyrazole derivative was obtained from the condensation of 2-deoxy-2-methylamino-D-glucose with ethyl acetoacetate (c.f. Vol.l4, p.89), the 3-substituted pyrrole analogues (72) were obtained from 1-deoxy-l-raethylamino-... 

The presence in plant materials of L-glucose, the enantiomorph of the ubiquitous D-glucose, has been reported (3) but needs confirmation. However, the natural occurrence of 2-deoxy-2-iV-methylamino-L-glucose in streptomycin and of 6-deoxy-3-0-methyl-L-glucose (L-thevetose) in certain cardiac glycosides has been established. 

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