N-Methyl-D-glucosamine

S Additional information <1-3, 5, 6, 7, 9> (<1, 3> D-fructose, D-mannose, D-maltose, D-galactose, N-acetyl-D-galactosamine, N-acetyl-D-mannosamine do not serve as substrates [1, 3] <2> N-methyl-D-glucosamine, D-glucosamine, N-acetyl-D-galactosamine, N-acetyl-D-mannosamine do not... 

Thus, the NMLGA branch of the streptomycin pathway remains a puzzle. Not even the direct precursor is known as yet it could be the 1-phosphates of D-glucose, D-glu-cosamine, N/ acetyl-D-glucosamine, or N-methyl-D-glucosamine. The last is suggested by... 

UDP-N-methyl-D-glucosamine phosphate, has been detected which is... 

It is possible that the water-filled a-LTX channel, which is relatively wide ( 10A at its narrowest (Krasilnikov and Sabirov 1992 Orlova et al. 2000), can pass small molecules. Indeed, a-LTX channels inserted in the membranes of synaptosomes, NMJ nerve terminals, and receptor-transfected COS7 cells appear to pass fluorescein (Stokes-Einstein radius, Re = 4.5 A) and norepinephrine (Re < 4 A) (Davletov et al. 1998 Rahman et al. 1999 Volynski et al. 2000), shown in Figure 2 for comparison with 8-hydrated calcium ion (Rc = 4.2 A) and the toxin channel. Analysis of impermeant cations commonly used in channel studies reveals that a-LTX channels are poorly permeable (Hurlbut et al. 1994) to glucosamine H+(Re = 4.6 A) and not significantly permeable (Tse and Tse 1999) to N-methyl-D-glucamine (Re = 5.2 A), thus limiting the pore diameter by 10 A. 

It was pointed out that N-methyl-L-glucosaminic acid nitrile was only the second nitrile in the sugar series to be isolated in the cyanohydrin reaction and that extension of the general procedure by which it was prepared should result in the isolation of other members. The nitrile of N-methyl-L-glucosaminic acid showed the same unusual mutarotation as does that of the lower-melting form of D-gluconic acid nitrile. Wolfrom and Thompson have noted that N-methyl-L-glucosaminic acid nitrile hydrochloride was a much more stable compound than the free base. 

Zeitler, R. Giannis, A. Danneschewski, S. Henk, E. Henk, T. Bauer, C. Reutter, W. Sandhoff, K. Inhibition of N-acetylglucosamine kinase and N-acetylmannosamine kinase by 3-O-methyl-N-acetyl-D-glucosamine in vitro. Eur. J. Biochem., 204, 1165-1168 (1992)... 

Hitose-Kumagai A, Yagiia A. Akamatsu N. tlDP-N-mcthyl-D-glucosamine-phosphatc. A possible intermediate of N-methyl-L-glucosamine moiety of str omycin. J Antibiot 1982 35 1571-1577. 

Jeanloz RW, Flowtas HM (1962) Isolation and synthesis of methyl ester-methyl a-glycoside of 3-P-D-glucurraiosyl-N-acetyl-D-glucosamine (hyalobiuronic acid). J Am Chem Soc 84 3030... 

TLC of the di-O-methyl tetroses [74], tri-O-methyl apiose [75], mycinose [76], and the methyl ethers of N-acetyl-D-glucosamine [77, 78] on silica gel G has been reported. The mono-O-methyl-fructoses are readily separated on boric acid impregnated silica gel G using n-butanol-acetone-water (40 + 50 + 10) [79, 80]. TLC of several methylated sugars on Magnesol containing calcium sulfate as binder has also been reported [56]. 

The biosynthesis of the N-methyl-L-glucosamine moiety of streptomycin from D-glucosamine by S.griseus has been studied. Addition of thymine to the culture medium stimulated formation of streptomycin, and the conversion of D-glucosamine to N-methyl-L-glucosamine. A novel UDP-aminosugar nucleotide intermediate,... 

The carbon 1 of the D-mannose is joined by glycosidic linkage to carbon 4 of the N-methyl-L-glucosamine moiety of streptomycin (Fried and Stavely, 1947, 1952). It is usually found to some extent in streptomycin-producing cultures of... 

Carbon atoms derived from N-methyl-L-glucosamine Labeled D-glucose administered ... 

Candy, D. J., N. L. Blumson, and J. Baddiley The biosynthesis of streptomycin incorporation of C-labeled compounds into streptose and N-methyl-L-glucosamine. Biochem. J. 91, 31 (1964). 

Silverman, M., and S. V. Rieder The formation of N-methyl-L-glucosamine from D-glucose by Streptomyces griseus. J. Biol. Chem. 235, 1251 (I960). 

Asoln. of -l-bromo-3,4,6-triacetyl-N-diphenylphosphoryl-D-glucosamine inabs. methanol shaken 1 hr. with Ag-carbonate and Ca-sulfate methyl 3,4,6-tri-... 

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