W-acetyl-D-glucosamine

Chitin is an abundant biopolymer, especially in Perth where the thriving Western rock lobster industry produces tonnes of waste, a good proportion of which is exoskeleton and rich in chitin. It has been our aim for some years to put this waste chitin to some good use and so, initially, we have set out to prepare epoxyalkyl glycosides based on W-acetyl-D-glucosamine and its oligomers, for example 60 and 61. It is hoped that molecules such as 60 and 61 will prove to be efficient inhibitors of chitinases, ubiquitous enzymes involved in many biological processes [42]. 

Although W-acetyl-D-glucosamine has inhibitory properties, it is apparently not phosphorylated. When AT-acetyl-D-glucosamine is added alone to ox-brain extracts, no carbon dioxide is produced. Yeast hexokinase... 

Acetyl groups of hyaluronate are, most probably, introduced into d-glucosamine 6-phosphate (see Section III, 3). This would be transformed to the W-acetyl-D-glucosamine units, which are then incorporated into the developing hyaluronate molecule. Although acetate exchange may take place with streptococcal hyaluronate, exchange probably does not occur in rabbit hyaluronate. 

When W-acetyl-D-glucosamine is heated with dilute sodium carbonate solution a colorless chromogen is formed. The latter yields a violet dyestuff with p-dimethylaminobenzaldehyde in acidic solution. This reaction is the basis of the quantitative determination of V-acetylamino sugars (Morgan-Elson reaction). 

D-Glucosamine is an example of an amino sugar. In many instances the amino group is acetylated as in W-acetyl-D-glucosamine. A/ Acetylmuramic acid is an important component of bacterial cell walls (Section 24.10). 

S3mthesis of 2, 3 -Epox3rpropyl 8-Glycosides of W-Acetyl-D-Glucosamine and of Its Oligomers... 

The former four are called homopolysaccharides since the fimdamen-tal sugar repeating unit is of the same structure o-glucose is linked via a j6(l 4) glycosidic bond in cellulose and a(l 4) in amylose, xylose and W-acetyl-D-glucosamine being via 4) in xylan and chitin, respectively. 

W-Acetyl-D-glucosamine 47 Aloe-emodol 3724 2-Amino-3-hydroxypropanoic acid. ... 

Scheme 11 Possible intermediates involved in the reaction of Af-acetyl-D-glucosamine (66) and W-acetyl-D-mannosamine (67)...

Miller, W.L., Wenzel, C.Q., Daniels, C., Larocque, S., Brisson, J.-R., Lam, J.S. Biochemical characterization of WbpA, a UDP-N-acetyl-D-glucosamine 6-dehydrogenase involved in O-antigen biosynthesis in Pseudomonas aeruginosa PAOl. J Biol Chem 279 (2004) 37551-37558. 

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. 

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)... 

Kuk, J. H., Jung, W. J., Jo, G. H., Ahn, J. S., Kim, K. Y, and Park, R. D. 2005. Selective preparation of AJ-acetyl-D-glucosamine and AJJV -diacetylchitobiose from chitin using a cmde enzyme preparation from Aeromonas sp. Biotechnol Lett 27 7-11. 

Shibata, Y, Foster, L. A., Metzger, W. J. et al. 1997b. Alveolar macrophage priming by intravenous administration of chitin particles, polymers of IV-acetyl-D-glucosamine, in mice. Infect. Immun. 65 1734-1741. 

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