Glucosamine structure

Symington FW, Fenderson BA, Hakomori S. Fine specificity of a monoclonal anti-testicular cell antibody for glycolipids with terminal A-acetyl-o-glucosamine structure. Mol Immunol 1984 21 877-882. 

Fig. 26.1.1. Abbreviated biosynthetic pathway of the monomeric N-acetyl-glucosamine structure of chitin starting from trehalose.

However, Park et al. (2004) reported that chitosan process anticoagulant activity was tested in vitro. They hypothesized that blood coagulation factors in the presence of chitosan with a glucosamine structure might be dependent in terms of degree of deacetylation, molecular size, and other physical characters. 

Another structural variation is the replacement of a hydroxyl group m a carbohydrate by an ammo group to give an ammo sugar The most abundant ammo sugar is one of the oldest and most abundant organic compounds on earth N Acetyl d glucosamine is the... 

Recently, Li et al. [30], Yu et al. [31] reinvestigated the mechanism of graft copolymerization of vinyl monomers onto carbohydrates such as starch and cellulose initiated by the Ce(IV) ion with some new results as mentioned in Section II. Furthermore, they investigated the mechanism of model graft copolymerization of vinyl monomers onto chitosan [51]. They chose the compounds containing adjacent hydroxyl-amine structures, such as D-glucosamine, /mn5-2-amino-cyclohexanol, 2-... 

In spite of the alteration due to deacetylation, chitosan from crab tendon possesses a crystal structure showing an orthorhombic unit cell with dimensions a = 0.828, b = 0.862 and c = 1.043 nm (fiber axis). The unit cell comprises four glucosamine units two chains pass through the unit cell with an antiparallel packing arrangement. The main hydrogen bonds are 03 05 (intramolecular) and N2 06 (intermolecular) [82]. This material has also found medical uses (below). 

Figure 48-9. Structure of heparin. The polymer section illustrates structural features typical of heparin however, the sequence of variously substituted repeating disaccharide units has been arbitrarily selected. In addition, non-O-sulfated or 3-0-sulfated glucosamine residues may also occur. (Modified, redrawn, and reproduced, with permission, from Lindahl U et al Structure and biosynthesis of heparin-like polysaccharides. Fed Proc 1977 36 19.)...

Richy F, Bruyere O, Ethgen O, et al. Structural and symptomatic efficacy of glucosamine and chondroitin in knee osteoarthritis A comprehensive meta-analysis. Arch Intern Med 2003 163 1514-1522. 

Final proof of the structure of D-glucosamine as 2-amino -D-gluco-pyranose (I) was furnished as indicated below independently by both chemical14, 16 and x-ray methods.1 By the action of ammonia on 2,3-... 

Both methods of approach moreover proved that a series of methylated derivatives of D-glucosamine described by Cutler, Haworth and Peat,14 and most useful as reference compounds in this field, were all of the pyranose configuration. Further proof of the pyranose structure of methyl D-glucosaminide and methyl N-acetyl-D-glucosaminide was pro-... 

From the identification of these products it was possible to give a means of portraying the type of structure (LVIII) present in the carbohydrate molecule. In this, by glycosidic attachment, seven N-acetyl-D-glucosamine unitB and one D-galactose unit radiate from a central core of three D-mannose units. It is not yet clear by what linkages the d-mannose units are mutually attached, or to which D-mannose the d-galactose residue is linked. 

The structure of the new product from D-glucosamine has also been confirmed by Muller and Varga,7 who oxidized the compound (obtained by Garda Gonz lez) with lead tetraacetate and isolated ethyl 5-formyl-2-methyl-3-pyrrolecarboxylate (XXII), the melting point and other properties of which agreed with those of the compound described by Fischer and Schubert.24... 

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