Glucuronic acid chemical synthesis

Mehltretter, C. L., The Chemical Synthesis of D-Glucuronic Acid, VIII, 231-249... 

In the present chapter, the more significant methods which have been reported for the chemical synthesis of D-glucuronic acid will be described and discussed. They are reductive and oxidative procedures and will be... 

Sowden82 recently has prepared D-glucuronic acid isotopically labeled at carbon atom 6 for certain chemical and biochemical studies. In this novel synthesis, 5-aldehydo-l,2-isopropylidene-D-xylofuranose88 (XVI), prepared by periodate cleavage of 1,2-isopropylidene-a-D-glucofuranose (XV), was condensed with Cu-labeled sodium cyanide. Alkaline... 

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... 

Glucose. See also, Dextrose, biosynthesis of aromatic compounds from D-, 15, 235-270 methyl ethers of D-, 6, 145-190 Glucuronic acid, D-, chemical synthesis of, 8, 231-249 conjugates of, of animal origin, 9, 185-246... 

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. 

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