Uronic chemical synthesis

Compounds known to behave in this way in vivo are listed in recent reviews in this Series.1 2 The structures of some of the /3-D-glucopyranosiduronic acids isolated from urine have been proved by chemical synthesis.3 A few similar derivatives of flavones and triterpenes have been isolated from plants. D-Glucuronic acid also occurs in mammalian tissues as a constituent of acid mucopolysaccharides (aminodeoxypolysaccharides, containing uronic acid), such as hyaluronic acid, chondroitinsulfate, and heparin,4 and it is a direct precursor of L-ascorbic acid in plants and mammals.6 It is present in many of the plant polysaccharides classified as hemicelluloses6 and gums,7 and it has also been found in certain bacterial polysaccharides.4... 

This article must, by its very nature, be regarded as no more than an interim report. Clearly, there are still many features of the chemistry of these compounds which require further elucidation, as, for example, the behavior of the compounds as carboxylic acids, their analogy with the uronic acids, and their ease of lactonization. To date, progress has been greatly hindered because of the difficulties encountered in assigning the correct formulas and structures to these various acids, but it is to be hoped that further research will soon lead to a further characterization of these compounds and then to their complete, chemical synthesis. 

Yoshikawa M, Kamigauchi T, Ikeda Y, Kitagawa I (1981) Chemical transformation of uronic acids leading to aminocyclitols. IV. Synthesis of hexaacetyl-streptamine from N-Acetyi-D-glucosamine by means of electrolytic decarboxylation. Chem Pharm Bull 29 2582-2586... 

---