Glucosamine 3-amino-3-deoxy

The phosphorylation of D-glucosamine (2-amino-2-deoxy-D-glucose) was first achieved by incubating it with brain extracts and ATP.266 Crystalline, yeast hexokinase plus ATP also phosphorylates D-glucosamine, to give the 6-phosphate, at a rate at least 75 % of that of phosphorylation of D-glucose ... 

The most common amino sugars are o-Glucosamine (2-amino-2-deoxy-D-glucose)... 

Amino sugars are widely distributed naturally and include molecules such as D-glucosamine (2-amino-2-deoxy-D-glucose), D-galactosamine (2-amino-2-deoxy-D-galactose), and sialic acid, a derivative of D-mannosamine (2-amino-2-deoxy-D-mannose). 

PROBLEM 22.33 Glucosamine (2-amino-2-deoxy-D-glucopy-ranose) is a very important substituted sugar. It is often used for the treatment of osteoarthritis. Draw the P form of glucosamine. 

Amino-sugars and Related Compounds. Part II. Observations on the Acidic Hydrolysis of Derivatives of 2-Amino-2-deoxy-D-glucose (D-Glucosamine), A. B. Foster, D. Horton, and M. Stacey,... 

Reactions of 2-(2, 4 -Dinitrophenyl)-amino-2-deoxy-r>-glucose, (DNP-D-glucosamine), and derivatives, P. F. Lloyd and M. Stacey, Tetrahedron, 9 (1960) 116-124. 

Amino-2-deoxy-a-D-glucose (a-D-Glucosamine) from Crustacean Shell, M. Stacey and J. M. Webber, Methods Carbohydr. Chem., 1 (1962) 228-230. 

Lactosediamine (LacdiN) 2-Amino-2-deoxy-P-D-galactopyranosyl-(1 -44)-D-glucosamine... 

O-Methyl-D-glucosamine Hydrochloride (2-Amino-2-deoxy-6-0-methyl-... 

In a study of the oxidation of 2-amino-2-deoxy-D-glucose (D-glucosamine) derivatives, Neuberger12 obtained better results using sodium metaperiodate (at its accompanying pH of 3 to 4) than with periodic acid at lower pH values and a pH of 4.5 was found by Jeanloz and Forchielli78a to be optimal for these derivatives. 

The reaction of 2-amino-2-deoxy-D-glucose (D-glucosamine) with a dicarbonyl compound was carried out for the first time by Pauly and Ludwig,91 who were trying to discover how pyrrole rings in natural products are formed. They heated free D-glucosamine and ethyl acetoacetate on a steam bath and obtained a substance in which the presence of the pyrrole ring was demonstrated by the pine-splinter test. 

Amino-2-deoxy-D-glucose (D-glucosamine) H H HO H HOHjC—C—C—C—C—CHO HO HO H nh2 widespread in animals, fungi, and bacteria... 

Procedure Synthesis of Xylonic, Galactonic, Mannonic, 2-Deoxygluconic Acid and Synthesis of 2-Amino-2-deoxy-gluconic Acid (Glucosaminic Acid)... 

The Knovenagel condensation under basic conditions was first investigated with D-glucosamine chlorhydrate (28.HC1) as the sugar. The condensation of this reducing amino sugar with pentane-2,4-dione 1 in aqueous acetone in the presence of sodium carbonate afforded the pyrrole derivative 29 in 85% yield [99] (Scheme 5). The reaction was extended to other 2-amino-2-deoxy-aldose and carbon nucleophiles [100-104]. 

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. 

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