Glucosamine applications

Hashizume, T, Yonehara, K., Ohe, K. and Uemura, S., A novel amphiphilic chiral hgand derived from d-glucosamine. Application to palladium-catalyzed asymmetric allylic substitution in an aqueous or organic medium, allowing catalyst recycling, J. Org. Chem., 2000, 65, 5197. 

Since the synthesis of glycolipids involves the synthesis of both the lipid and the oligosaccharide portions, we shall also discuss that part of the recorded lipid synthetic work which has involved the use of carbohydrates. In fact, some of the first-recorded applications of carbohydrate molecules as chiral templates are to be found in the lipid field particularly with the use of 1,2 5,6-di-O-isopropylidene-D-mannitol [33] as a precursor of chiral glycerol derivatives for the synthesis of phospholipids and glycolipids based on glycerol and with the use of glucosamine derivatives for the synthesis of phytosphingosines [34] and since this area has not previously been reviewed, it will be treated with a more historical perspective. 

The presence of hexosamine in the hydrolyzate of a mucopolysaccharide may well be indicated on the basis of the above colorimetric tests and the amount present estimated. The identity of the amino sugar cannot thereby be established, since the colorimetric methods cannot differentiate between glucosamine, chondrosamine or any other 2-amino sugar. The ideal means for the identification of a hexosamine is the isolation of a well characterized crystalline derivative. Numerous compounds for this purpose or of potential application have been recorded in the literature but only in the case of the Schiff s bases have satisfactory results been obtained. 

The application of chromatographic techniques to the analysis of mucopolysaccharides has provided a new impetus in the structural study of these substances and has opened up new fields of research. The behavior of glucosamine on ion-exchange resins was early examined by Freudenberg, Walch and Molter71 and the amino sugar has been separated... 

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