Glucuronic acid chemistry

As the chemistry of D-glucuronic acid and its glycosides has already been reviewed,6 the present article is restricted to discussion... 

D8. Dutton, G. J., The biosynthesis of glucuronides. In Glucuronic Acid. Free and Combined. Chemistry, Biochemistry, Pharmacology, and Medicine (G. J. Dutton, ed.), pp. 185-299. Academic Press, New York, 1966. 

J. C. Gonzalez, S. Garcia, S. Bellu, J. M. Salas-Peregrin, A. M. Atria, L. Sala, and S. Signorella, Redox and complexation chemistry of the Crvl/Crv/Crlv-D-glucuronic acid system, Dalton Trans., 39 (2010) 1-14. 

Fractionation and Chemistry of Citrus Pectic Polysaccharides. Pectic polysaccharides, commonly known as pectin, appear early in plant cell-wall formation. A series of complex biochemical steps results in the formation of cell plates followed first by its growth in area (primary cell wall) then in thickness (secondary cell wa.ll). Exclusive of randomly oriented cellulose fibrils, primary cell wall is composed mainly of pectic polysaccharides (34). These pectic polysaccharides are rich in D-galacturonic acid, D-galactose and L-arabinose residues. With growth in thickness of cell wall (secondary cell wall),there appears to be a replacement of pectic polysaccharide deposition with polysaccharides rich in D-glucuronic acid or 4-0-methyl-D-glucuronic acid,... 

III. Chemistry of the Conjugates of d-Glucuronic Acid 1. General Properties... 

Many important natural products are (formerly) derived by chain elongation at position 5 of pentoses, or at position 6 of hexoses. Uronic acids, which are easily prepared, can be converted into the 4 radical 90 by chemistry based on the thiohydroxamate 6.77 We postulated that, if the hindrance on the a-side of the molecule was great enough, the carbon-carbon bond formed by reaction of 90 with a suitable radicophilic olefin would be the natural / -bond. In fact, even a dimethyl-ketal as in 90 (B = natural base or protected derivative thereof) was sufficient to direct the bond formation very largely to the desired face.77 The diacetone ketal of glucuronic acid 91 upon conversion to its iV-hydroxy-2-thiopyridone derivative 92 and then photolysis in the usual way in the presence of methyl acrylate gave the expected derivative 93 as a mixture of... 

Methods in Structural Polysaccharide Chemistry, 15, 53-89 Brady, Robert F., Jr., Cyclic Acetals of Ketoses, 26, 197-278 Bray, H. G., D-Glucuronic Acid in Metabolism, 8, 251-275... 

Finally, Hirst s later contributions to monosaccharide chemistry must not be overlooked. With E. G. V. and Elizabeth Percival, four different trimethyl, 3,4- and 4,5-dimethyl, and the 4-methyl ethers of D-fructose were synthesized from isopropylidene derivatives having well established structures. Certain methyl ethers of D-mannuronic acid and D-glucuronic acid were also prepared, and their periodate oxidation was compared with that of related ethers of D-galacturonic acid. With Elizabeth Percival, he also contributed articles on the methyl ethers of mono- and di-saccharides, and on glycofuranosides from cyclic carbonates, to Methods in Carbohydrate Chemistry, Vol. 2 (1963). 

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