Glycosylamine uronic Acids

Heyns and coworkers have shown that D-glucuronic acid and its potassium and sodium salts react much more rapidly than D-glucose with primary and secondary arylamines,303,304 aliphatic amines,305 and the amino group of an amino acid,305 306 in aqueous or alcoholic media, to 

As part of a study of a series of glycosylureides, Micheel and Haben-dorff212 treated methyl (2,3,4-tri-O -acetyl-/3-D-glucopyranosy 1 thio-cyanate)uronate with methanolic ammonia at 0°, and obtained, by way of the (nonisolated) isothiocyanate 105, the crystalline thiourea derivative 106 in 91.8% yield the structure assigned to 106 was supported 

Reactions between D-glucuronic acid, its amide, or 6,3-lactone with various aromatic and aliphatic amines, carbamates, and their derivatives, have often been used for the preparation of (D-glucosyl-amine)uronic acid derivatives of interest as potential drug metabolites or chemotherapeutic agents however, very little evidence is available 

Despite extensive studies, the enzymic formation of (D-glucosyl-amine)uronic acids as a result of the transformation of amino compounds in vivo, and the susceptibility of this type of conjugate towards hydrolysis by /3-D-glucosiduronase, are still the subject of controversial results. It should be emphasized that the high lability of (D-glucosyl-amine)uronic acids in general, and the lack of adequately characterized, synthetic model-compounds, create problems in obtaining reliable results. 

A (D-glucosylamine)uronic acid derivative has been identified331 as the metabolite of carbamazepine (5//-dibenz[fe,/]azepine-5-carbox-amide, an anti-epileptic agent) by means of permethylation, g.l.c., and mass spectometry. Analytical data for the conjugate (identified in the bile of the isolated, perfused, rat liver) indicated that the carboxamide nitrogen atom is linked to C-l of the sugar moiety. 

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The literature on /3-D-glucosiduronic acids is particularly voluminous, and the subject has been extensively reviewed from several aspects. Section III, dealing with this class of compounds, is devoted more to a general overview of their preparation, characterization, and reactions than to individual members. On the other hand, the categories of 1-esters of glycuronic acids and of (glycosylamine)uronic acids, which appear not to have been treated previously as separate topics, receive relatively more attention. 

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