IV-Acetyl-D-glucosamine

EC 2.4.1.90 /V-Acetyllactosamine synthase UDP-galactose + iV-acetyl-D-glucosamine UDP Af-acetyllactosamine Golgi apparatus ... 

IV-Acetyl-D-glucosamine (30.g, 0.135 mol) is dissolved in concentrated hydrochloric acid (120 mL), and tedmica] grade ethanetinal (120 mL) is added in a stoppered flask at OX. The reaction is stined at that temperature for 24 hand then neutralized with exees basic lead carbonate (700 g). The mixture is diluted with water (500 mL), and the solids are filtered and washed with Water (1L). After evaporation of the combined filtrate and washings, the resultant residue is crystallized from methanol-ether (36 g, 81%). Further recrystallization from methanol-chloroform-ether gives pure product mp 129.5-130.5°C, [< ] —35° (c 4, water). 

Chitin is a polysaccharides with the exact same structure as cellulose but containing iV-acetyl-D-glucosamine or D-glucosamine and are fairly widely distributed [76] (see O Fig. 6 for the structure of a segment of chitin). It is a structural polysaccharide that forms fibers, is water impermeable, and replaces cellulose in the cell walls of many species of lower organisms. 

A large number of bacterial polysaccharides are known [104]. The major structural component of the bacterial cell wall is a polysaccharide, known as murein and composed of a repeating unit of one A-acetyl-D-glucosamine and an O-lactyl substituted IV-acetyl-D-glucosamine (A-acetyl-D-muramic acid) see Sect. 7.3. 

The 5-thio analogue of iV-acetyl-D-glucosamine (35) was synthesized from suitably protected furanoid [60,61,62] or open-chain [63] D-glucosamine derivatives employing the general approach via the thiirane route as well as from 5-thio-D-glucal (36) [64] via azi-donitration [65,66]. 

D-glucosamine preparation. This labile phosphate derivative is inactive as a substrate. Since the d anomer of D-glucosyl phosphate is more acid-labile than is the a anomer/ the a anomer of iV-acetyl-D-glucosamine 1-phosphate is considered to be involved in this reaction. ... 

Pig-kidney extracts have some phospho-iV-acetyl-D-glucosamine mutase activity. The ratio of phosphoglucomutase to phospho-AT-acetyl-n-glucos-amine mutase activity is 60 1 in these extracts. In rabbit muscle, this ratio i is 1200 1. Phosphoglucosamine mutase activity was not checked in any of the phosphomutase preparations investigated by this worker. 

D-Glucosamine 6-phosphate can be readily acetylated by a AT-acetylase obtained from a preparation of yeast hexokinase. The resulting iV-acetyl-D-glucosamine 6-phosphate is identified by its Morgan-Elson reaction. The acetyl-coenzyme A which appears to be required for this reaction may be generated by acetate, adenosine-5-triphosphoric acid, and coenzyme A (in the presence of an acetate-activating enzyme). 

Uridine-5-triphosphoric acid - - iV-acetyl-D-glucosamine 1-phosphate... 

A. M. Katzin and W. Colli, Lectin receptors in Trypanosoma cruzi. An iV-acetyl-D-glucosamine-containing surface glycoprotein specific for the trypomastigote stage, Biochim. Biophys. Acta., 727 (1983) 403 -11. 

Treatment of iV-acetyl-D-glucosamine with dilute alkali is reported to give 3-ace-tamidofuran 192 (R1 = R2 = R3 — 11, R4 = Me) (56CB1473). An imine derivative of 3-aminofuran has been obtained by reaction of 3-furyllithium with the oxime 0-tosylate of tetraphenylcyclopentadienone (84JA5753). 

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