Glucose 2-deoxy-2-methylamino

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. 

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... 

A methylation analysis of S14, performed in the authors laboratory,44 gave 2,3,4,6-tetra-O-methyl-D-galactose, 2,4,6-tri-O-methyl-D-galactose, and 2,3,6-tri-O-methyl-D-glucose in the proportions 1 1 1. Although these are the same components as previously reported, the proportions are different. In addition to these sugars, 2-deoxy-3-0-methyl-2-(methylamino)-D-glucose was also obtained. 

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. 

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-... 

Gorin and Magus investigated the use of the trimethylsilyl derivatives of the methyl ethers of 2-deoxy-2-(methylamino)-D-glucose and the corresponding n-galactose compounds. 

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. ... 

Metal complexes of 2-deoxy-2-methylamino-D-glucose and other amino-hexoses have been studied and stability constants derived. ... 

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-... 

Degradation of the antibiotic sporaviridin has yielded two further pentasaccharides, viridopentaose A and C, which are closely related to viridopentaose B mentioned in last year s report (see Vol. 13, p. 158) viosamine is replaced by the corresponding simple sugars 6-deoxy-D-glucose and -D-glucose, respectively. N.m.r. evidence indicates that the acidic antitumour antibiotic neocarzinostatin contains 2,6-dideoxy-2-methylamino-galactose as a component of a chromo-phor attached to protein. ... 

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

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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