Glucosamine 2-acetamido-2-deoxy

D-Giucosamine (Chitosamine) (2-Amino-2-deoxy-D-glucose) and /V-acetyl-D-glucosamine (2-Acetamido-2-deoxy-D-glucose)... 

Chitin (poly-A-acetyl-D-glucosamine, 2-acetamido-2-deoxy-1,4-P-D-glucan) is one of the three most abundant polysaccharides (along with starch and cellulose) and is extracted from shells of crustaceans and cell walls of fungi. Chitosan is produced by deacetylation of chitin and can be spun into fibres, cast into films, or precipitated in a variety of micro-morphologies. Major applications are in biomaterials, pharmaceuticals, cosmetics, metal ion sequestration, agriculture and the food industry. ... 

Chitin is a polysaccharide found in the outer skeleton of crustaceans, insects, crabs, shrimp, lobsters, in the internal structures of other invertebrates, and in the ceU walls of fungi. Chitin (poly-N-acetyl-d-glucosamine, 2-acetamido-2-deoxy-l,4-P-d-glucan) (Figure 11.6) is one of the three most abundant polysaccharides in nature, is biodegradable, non-toxic, and readily biocompatible. 

The anion of nitromethane adds easily to the carbonyl functions of sugars. This is a useful strategy for extension of the carbon chain.100 2-Acetamido-2-deoxy-P-D-glucose (A-acetyl-D-glucosamine) is the carbohydrate unit of glycoproteins that occurs most often. The nitromethy-lation method provides a straightforward route to a series of C-glycosyl compounds with the acetamido functionality (Eq. 3.62).101... 

Suitable material is available from Pfanstiehl Laboratories, Waukegan, Illinois. It may also be prepared from the hydrochloride of 2-amino-2-deoxy-D-glucose (D-glucosamine) in 95% yield by the facile procedure of Inouye and co-workers.2 The 2-acetamido-2-deoxy-D-glucose should be dried at 25° (1 mm.) for at least 12 hours before use. If this material is in the form of a powder rather than compact crystals, more acetyl chloride... 

Both anomers of 2-acetamido-2-deoxy-D-glucopyranosyl phosphate have been prepared previously however, the methods used are not easily adapted to obtain glucosamine derivatives carrying 3-hydroxytetradecanoic acid attached to the amino group. 

The synthesis of this substance, starting with methyl 2-acetamido-4,6-0-benzylidene-2-deoxy-a-D-glucoside, was performed as follows. The two isomers which were formed were separated on a Dowex 50 colunm, and one (Md +109°) was shown to be identical with natural muramic acid. The strong dextrorotation effectively ruled out the L-glucosamine configuration, and the configuration of the lactic moiety was deduced to be most likely d. The second isomer had [ ] +52° and differed, in its behavior on resin columns and in paper chromatography, from natural muramic acid. 

Bognar, R, Herczegh, P, Whistler, R L, Madumelu, E B, 2-Acetamido-2-deoxy-5-thio-D--glucopyranose (5-thio-A-acetyl-D-glucosamine), Carbohydr. Res., 90, 138-143, 1981. 

Biosynthetic investigations show that the hyaluronate chain is assembled by the alternate incorporation of preformed A -acetyl-n-glucosamine and D-glucuronate units. In descriptive scientific nomenclature, the units are 2-acetamido-2-deoxy-/3-D-glucopyranosyl and /3-D-glucopyranosyluro-nate, respectively. 

The first preparation of a 4,6-dimethyl ether of 2-amino-2-deoxy-D-glucose was reported by Haworth, Lake, and Peat. Action of ammonia on methyl 2,3-anhydro-4,6-di-0-methyl-j3-D-mannoside, followed by N-acetylation of the product, led to the formation of methyl 3-acetamido-3-deoxy-4,6-di-0-methyl- S-D-altroside (in high yield) and of methyl 2-acetamido-2-deoxy-4,6-di-0-methyl- S-D-glucoside (in a 9.4% yield). Methylation of the latter compound yielded a 3,4,6-trimethyl ether identical with the one prepared from natural n-glucosamine. ... 

A convenient synthesis of unprotected 2-acetamido-2-deoxy-P-D-glucopyranosides 149 from A-acetyl-D-glucosamine 147 has been achieved by treatment of the reactive furanosyl oxazoline 148 with a variety of alcohols under acidic conditions <050L4021>. 

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