2-Acetamido-2-deoxy-D-glucopyranose

Acetamido-2-deoxy-D-galactopyranose (—), and 2-Acetamido-2-deoxy-D-mannopyranose ( ) at Anomeric Equilibrium in Aqueous Solution (redrawn from Ref. 28), and 2-Acetamido-2-deoxy-D-glucopyranose (- -) at Anomeric Equilibrium in Aqueous Solution. (Redrawn from Ref. 29.)... 

Fig. 18.—The Circular Dichroism of a 2-Acetamido-2-deoxy-D-glucopyranose Film. (Redrawn from Ref. 37.)...

Figure 7.34 Synthesis of 2-acetamido-2-deoxy-/3-D-galactopyranosyluronic acid-(l —> 4)-2-acetamido-2-deoxy-D-glucopyranose...

Warren and associates (18) have prepared a glycosyl azide derivative (15) of a heptasaccharide. This glycosyl azide was obtained from O-a-D-manno-pyranosyl-( 1 — 6)-0-[a-D-mannopyranosyl-( 1 — 3)-(9-a-D-mannopyrano syl-(l— 6)-0-a-D - mannopyranosyl - (1 — 3)] - O-fi- d - mannopyranosyl -(1 — 4) - O - (2 - acetamido - 2 - deoxy-/ -d-glucopyranosyl) - (1 — 4) - 2 -acetamido-2-deoxy-D-glucopyranose (12) by treatment of its peracetylated derivative 13 with trimethylsilyl trifuoromethanesulfonate, followed by reaction of the intermediary oxazoline 14 with trimethylsilyl azide. Reduction of the glycosyl azide 15 in the presence of Lindlar catalyst gave the glycosyla-mine derivative 16. The condensation of 16 with 1-tert-butyl N-(9-fluoren-... 

Acetamido-2-deoxy-D-glucopyranose (4 85 g) was dissolved in water (400 mL) the pH of the solution was adjusted to 11 with 5 M sodium hydroxide and the solntion was left for 1 day at room temperature. The mixture was deionized with Dowex 50-X8 (H+) resin and evaporated to dryness under vacuum. The residue was taken up with ethanol (300 mL) and heated on the steam bath with stirring. On cooling 4 crystallized (66 g) the mother liquor was concentrated, and a second crop of 4 (5 g) was obtained. Concentration of the second mother liquor gave a third crop (3.5 g) of 4. The recovered 4 was re-treated in the same way. Both residual syrups afforded a mixture of 4 and 5 (17.1 g) containing 88% of 5 according to NMR-spectral analysis. 

The most important derivative of chitin is chitosan obtained by partial deacetylation of chitin in the solid state under alkaline conditions or by enzymatic hydrolysis in the presence of a chitin deacetylase. The ratio of 2-acetamido-2-deoxy-D-glucopyranose to 2-amino-2-deoxy-D-glucopyra-nose moieties determines the identity of the product, that is, chitin or chitosan [9]. The published methods used for the production of chitosan from chitin are summarized in Table 2.3. 

Vetere A, Galateo C, Paoletti S. All-aqueous, regiospecific transg-lycosylation synthesis of 3-0-alpha-L-fucopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a building block for the synthesis of branched oligosaccharides. Biochem. Biophys. Res. Commun. 1997 234 358-361. 

Y. Nishida, H. Hori, H. Ohrui, and H. Meguro, Carbohydr. Res., 170, 106 (1987). H-N.M.R. Study on (6S)-(6- Hi)-2-Acetamido-2-deoxy-D-glucopyranose and Conformational Analysis of 2-Acetamido-2-deoxy-D-glucopyranose. 

Enzyme Inhibition - 2-Acetamido-2-deoxy-D-glucopyranose, chitobiose and chitotriose were P-glycosidically linked to various exo-glycosidase inhibitors, and evaluated as chitinase inhibitors. Good inhibition was found for an JV-formyl-pyrrolidine analogue (transition state mimic) and epoxybutyl chitobioside (an irreversible inhibitor). ... 

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