D-Glucosylamine

From Scheme 2, it may be seen that D-glucosylamine and D-fructo-sylamine are also considered to be intermediates in the formation of heterocyclic compounds. This intermediary formation of 1-amino-1-deoxy-D-fructose and D-glucosylamine from D-glucose and am-... 

The rate constants kr and k2 have values of 20 X 10-3 and 22 X 10-3 min-1, respectively, in 2 M hydrochloric acid at 100°, and the overall rate of decomposition of 2-acetamido-l-N-/3-L-aspartyl-2-deoxy-/3-D-glucosylamine occurs with a rate constant of 42 X 10-3 min-1, that is, a half-life of the order of 17 minutes.92 L-Aspartic acid and ammonia are released at the same rate.92-95... 

An experiment whose results support certain mechanistic views (see Section VI, p. 110) was the ammonolysis of 2,3,4,6-tetra-O-benzoyl-D-glucopyranosylamine,30 which afforded a mixture of D-glucose and D-glucosylamine in 95% yield, and only 1.4% of l,l-bis(benzamido)-l-deoxy-D-glucitol (17) with traces of N-benzoyl-D-glucopyranosylamine. 

For the N-acylaldobiosylamines, this method requires a second oxidation and further reduction, as shown for N-acetyl-6-O-a-D-galactopyranosyl-/3-D-glucosylamine (N-acetyl-/3-meIibiosylamine)49 (54) in the following sequence. 

Another possible mechanism7 for the transformation of sugars with amino acids into colored products is through the Amadori rearrangement,44 which is the isomerization of an aldosylamine to a ketose derivative, for example, of a D-glucosylamine derivative to a derivative of 1-amino-l-deoxy-D-fruc-tose. Such a conversion has been shown to occur when an amino acid reacts... 

Oxidation of N-Acetyl-D-glucosylamine.98 Six grams (0.027 mole) of N-acetyl-D-glucosylamine (XLI) in 100 cc. of water is added to 18.5 g. (0.081 mole) of paraperiodic acid in 100 cc. of water, and the reaction mixture is maintained at 25° for four and one-half hours, which is known from analytical data obtained in small-scale experiments to be sufficient time for completion of the reaction with the consumption of two moles of the oxidant. The solution is exactly neutralized with barium hydroxide, the precipitate removed, and the filtrate evaporated to dryness in vacuum. The solid is extracted with 100 cc. of absolute ethanol, the ethanol extract evaporated to dryness, the residue taken up in ethanol, and the solution is centrifuged and again evaporated to dryness. The product, the dialdehyde XLII, can be converted into the corresponding barium salt (see reference 93). 

N-Acetyl-D-glucosylamine (XLI). Acetamino-D-hydroxymethyl diglycolic aldehyde (XLII) " 93... 

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