Glucosylamines, Amadori rearrangement formation

A most interesting application having commercial value is the formation of surface-active derivatives by the condensation of hydrophilic sugars with fatty amines. Only Amadori rearrangement gave hydrolysis-resistant compounds, displaying a considerable decrease in the surface tension of water, in contrast to the glucosylamine derivatives. 

Indeed, hydrochloric acid failed to catalyze formation of l-deoxy-l-/ -tolylamino-D-finctose from A- -tolyl-D-glucosylamine in methanol at 100 °C, while all carboxylic acids tested gave 8-40% yields of the Amadori rearrangement product, and even better yields were provided by the respective carboxylate potassium salts." ... 

The most extensive part of this Section collects the Amadori compounds of D-fructose, that is, the l-amino-l-deoxy-n-fructoses. These substances, derivatives of the amino sugar isoglucosamine, are known to be rearrangement products of D-glucosylamines. Many problems, reviewed by Hodge (see Ref. 251), regarding their structure and possible mode of formation have been solved during the past few years. 

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