3-Amino-3-deoxy-D-glucose

Nojirimycin (5-amino-5-deoxy-D-glucose) is an antibiotic used in studies of the biosynthesis of glycoproteins. Write its open-chain and pyranose ring structures. 

In 1982, Vasella and Voeffray [196] presented a synthesis of (+)-nojirimycin (5-amino-5-deoxy-D-glucose) using the 1,3-dipolar cycloaddition of a d-mannose-derived nitrone to furan. The chiral source in that synthesis (d-mannose) is not recovered. Jager and Muller used... 

An aq. soln. of 5-amino-5-deoxy-l,2-0-isopropylidene-a-D-glucofuranose satd. with SO2 warmed 60hrs. at 35-40° on a water bath 5-amino-5-deoxy-D-glucose-1-sulfonic acid. Y 96%. S. Inouye et al., Tetrahedron 24, 2125 (1968). 

The C-5-O-trifyl group can be displaced by iodide that in turn can be displaced by azide, with overall retention of the configuration (reaction 4.119) to give 5-amino-5-deoxy-D-glucose and the synthesis of nojirimycin [112]. Nojirimycin readily looses water, forming the imine that can be reduced with sodium borohydride to give the stable product, dihydronojirimycin (reaction 4.119). 

The biosynthesis of the nucleoside skeleton of polyoxins has been studied using C- and C-labelled glucose, glycerate, and uridine substrates it was suggested that condensation of uridine as its 5 -aldehyde with phosphoenol pyruvate gives an octofuranuloseuronic acid nucleoside, which loses the two terminal carbon atoms by oxidative elimination followed by transamination to give the required uridyl-5-amino-5-deoxy-D-allofuranosyluronic acid structure. ... 

CN 2-([(]-(4-chJorobenzoy])-5-methoxy-2-methyl-l//-indol-3-yl]acet>i]amino]-2-deoxy-D-glucose... 

In a study of the oxidation of 2-amino-2-deoxy-D-glucose (D-glucosamine) derivatives, Neuberger12 obtained better results using sodium metaperiodate (at its accompanying pH of 3 to 4) than with periodic acid at lower pH values and a pH of 4.5 was found by Jeanloz and Forchielli78a to be optimal for these derivatives. 

In analogy with the deamination of aminocyclohexanes,17-21 it has been found that the deamination, with nitrous acid, of 2-amino-2-deoxyaldohexoses in which the amino group has an equatorial orientation leads to 2,5-anhydrohexoses, as exemplified by the deamination of 2-amino-2-deoxy-D-glucose (10) to 2,5-anhydro-D-mannose22-25 (11). 

Fus ani, N. Ejima, D. Matsunaga, S. Hashimoto, K. Itagaki, K. Akagi, Y. Taga, N, Suzuki, K. (1987) 3-Amino-3-deoxy-D-glucose an antibiotic produced by a deep-sea bacterium. Expo iaitia, 43,464-5. 

Die Umsetzung von 2-Amino-2-deoxy-D-(- -)-glucose oder alternativ 1-Amino-1-deoxy-D-fruc-tose mit 2-Ethoxy-acrylsaure-imid-methylester (in situ erzeugt aus 2-Ethoxy-acrylnitril mit Natriummethanolat) liefert 2-Acetyl-4(5 )-[l (R), 2( S),3( R), 4-tetrahydroxy-bulyl]-imidazol... 

An original approach to the analysis of amino sugars has been proposed, based on their reaction with nitrous acid and subsequent reduction of the products with borohydride.564 By this procedure, 2-amino-2-deoxy-D-glucose and 2-amino-2-deoxy-D-galactose are converted into 2,5-anhydrohexitols, whereas 2-amino-2-deoxy-D-mannose yields D-glucitol. This mixture is readily separated after trimethyl-silylation. 

Fermentation procedures for preparing uridine 5 -(2-acetamido-2-deoxy-a-D-glucopyranosyl pyrophosphate) have also been reported. One of them255 involves the cultivation of Helminthosporium sativum in the presence of 2-amino-2-deoxy-D-glucose and the antibiotic polyoxin the latter is an inhibitor of chitin biosynthesis. The other256 utilized the incubation of yeast cells with uridine 5 -phosphate in the presence of an excess of 2-amino-2-deoxy-D-glucose and inorganic phosphate.257... 

The intravenous injection of 2-amino-2-deoxy-D-glucose-14C into rats, and subsequent isolation of the uridine diphosphate N-acetyl-hexosamine fraction, has been suggested as a fast and convenient method for preparing small amounts of a mixture of radioactive uridine 5 -(2-acetamido-2-deoxy-a-D-gIucopyranosyl pyrophosphate) and uridine 5 -(2-acetamido-2-deoxy-a-D-galactopyranosyl pyrophosphate). 

This reaction has been compared81 with the nitrous acid deamination of 2-amino-2-deoxy-D-glucose attack by a bromonium ion could lead to an intermediate, alkyl-iodonium cation (2-C-I-Br) , which would decompose through nucleophilic attack by 0-5, which is antiparallel to the leaving group at C-2. 

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