Glucopyranosiduronic acids synthesis

P. Florio, R. J. Thomson, A. Alafaci, S. Abo, and M. von Itzstein, Synthesis of 8 4-P-d-glucopyranosiduronic acids as mimetics of 2,3-unsaturated sialic acids for sialidase inhibition, Bioorg. Med. Chem. Lett., 9 (1999) 2065-2068. 

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... 

Until recent years, the sole somce of /3-D-glucopyranosiduronic acids, and indeed of D-glucuronic acid itself, was the urine of animals fed with the appropriate aglycons, and in most instances the chemical synthesis in the laboratory has yet to be achieved. In some cases [for example, phenol-phthalein (mono-)j3-D-glucopyranosiduronic acid], laboratory synthesis still presents difficulties. 

The methods of synthesis of uronic acids by catalytic and nonspecific oxidation of sugars has been reviewed,and a study of the oxidation of octyl a-D-glucopyranoside to octyl a-o-glucopyranosiduronic acid by sodium hypobromite catalysed by some ruthenium complexes has been reported. The stability constants of metal ion-uronic acid complexes have been reviewed. ... 

Li K, Helm R (1995) A practical synthesis of methyl 4-O-methyl-a-D-glucopyranosiduronic acid. Carbohydr Res 273 249... 

The synthesis of some -D-glucopyranosiduronic acids of biochemical interest has not yet been achieved, and one must rely upon biosynthetic methods of preparation. 

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