2-Acetamido-2-deoxy-D-glucose

The Oxidation of Some Carbohydrate Derivatives using Acetic Anhydride - Methyl Sulphoxide Mixtures and the Pfitzner-Moffat Reagent. Facile Synthesis of 3-Acetamido-3-deoxy-D-glucose and 3-Amino-3-deoxy-D-xylose, J. S. Brimacombe, J. G. H. Bryan, A. Husain, M. Stacey, and M. S. 

Brimacombe, J S, Bryan, J G H, Husain, A, Stacey, M, Tolley, M S, The oxidation of some carbohydrate derivatives, using acid anhydride-methyl sulphoxide mixtures and the Pfitzner-Moffatt reagent. Facile synthesis of 3-acetamido-3-deoxy-D-glucose and 3-amino-3-deoxy-D-xylose,... 

Amino-3-deoxy-a-D-glucopyranosyl)-2-deoxystreptamine (88) was synthesized by Umezawa and coworkers and by Nakajima and coworkers. In both of the syntheses, the isopropylidene derivative (85) of l,3-di-IV-(benzyloxycarbonyl)-2-deoxystreptamine was prepared as a key intermediate. (It is noteworthy that protection of the trans hydroxyl groups was achieved by an acetal-exchange reaction. - ) Also, the tri-0-benzylglycosyl chloride (86) of 3-acetamido-3-deoxy-D-glucose ... 

Kanamycin B has also been synthesized by S. Umezawa et al. by coupling a suitably protected neamine (Table 2, 75) with 3-amino-3-deoxy-D-glucose. The synthesis of kanamycin C has been accomplished by the same researchers through the glycosylation of 4, 6 -isopropylidine-l,3,2 -tri-N-benzyloxycarbonylparomamine (Table 2, 78) with tri-O-benzylglycosylchoride, obtained from 3-acetamido-3-de-oxyglucose. 

The molecules are helices having a twofold screw-axis, with an axial rise per disaccharide residue of 9.45 A (945 pm). The axes of the chains are parallel, and about equally spaced, but are not further organized into crystalline arrays. A hydrogen bond was proposed between the OH-3 group of the 2-acetamido-2-deoxy-D-glucose residues and 0-5 of the D-galactose 6-sulfate residues. 

The repeat distance is 18.6 A (1.86 nm), with a meridional reflection on the first layer-line. A tetrasaccharide repeating-unit was favored. It was suggested that the linkage between the 2-acetamido-2-deoxy-D-glucose and D-glucuronic acid residues is alternately a-D-(l — 4) and /3-d-(1 — 4). 

A chemoenzymatic synthesis of di-, tetra-, and octavalent sialyl Lewis X ligands scaffolded on dendrimers has been reported (Scheme 67). 508 Hypervalent L-lysine cores with covalently attached 2-acetamido-2-deoxy-D-glucose residues were chemically prepared and enzymatically transformed into sialyl Lewis X-containing dendrimers using (3-(l— 4) ga-... 

The most important result, however, is the binding of the trisaccharide tri-N-acetylchitotriose, as the model proposed for substrate binding and enzymic hydrolysis is based on this compound. The three substituted /3-D-glucopyranose residues are labeled A, B, and C in Fig. 2. Two observations are the same as for 2-acetamido-2-deoxy-D-glucose residue C has the same binding as the /3-d anomer, and the resulting shift of amino acid residue 62 (L-tryptophan) is 0.75 A. The hydrogen bonds between lysozyme and carbohydrates A and B are shown in Fig. 2 and listed in Table IV. Residue A, which is located... 

Release of 2-Acetamido-2-deoxy-D-glucose from Glycoproteins and Glycopeptides (GP) by Use of 2-Acetamido-2-deoxy-/3-D-glucosidase... 

Halide 32 was used first, in nitromethane-benzene solution in the presence of an equimolar proportion of mercuric cyanide. It was found83 that 32 gave a disaccharide at 0-6 of a protected derivative of 2-acetamido-2-deoxy-D-glucose in good yield, with a certain degree of stereoselectivity (a /3 ratio 7 3). Complete stereospecificity was attained, leading to the desired a-linked disaccharides, when the partially acylated bromide 33 was condensed with a number of different nucleophiles.66,83,84,93-95 A mechanism was postulated83 to explain the... 

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