D-Glucuronic acid lactone

A similar approach had been described for the synthesis of the mycotoxin patulin (2,3-pyranose-fused unsaturated lactone) from a 2-arabinopyranos-2-uloside derivative,16 and more recently, for the synthesis of a potent germination stimulant and some analogous compounds from D-xylose or commercially available D-glucuronic acid y-lactone.17... 

Such lactones had already been exploited in Rennes by Ferrieres et al. for the stereoselective formation of alkyl furanosides from the readily available D-glucuronic acid 20.27 Similarly, the analogous... 

Anhydro-L-gulono-1,4-lactone (62) was prepared100 in 62% yield by the platinum-catalyzed oxidation of 1,4-anhydro-D-glucitol. Methyl 3,4,5-tri-0-acetyl-2,6-anhydro-L-gulonate (63, R = H) was obtained from D-glucuronic acid by way of the tetraacetate (63, R = OAc) and the thioglycoside101,102 (63, R = SPh) (76%), followed by reduction in the presence of Raney nickel to afford 63 (R= H) (68%). 

Scheme 3.3 Chemoenzymatic conversion of D-glucuronic acid to L-ascorbic acid [59] NADPH-dependent uronate reductase A from Saccharomyces cerevisiae, cloned into . coli converted D-glucuronic acid at 90% yield. Chemical lactonization gave inter-...

The quantitative determination of uronic acids in polysaccharides is complicated by lactonization, and these problems have been carefully examined by Blake and Richards.26,98 In the course of these studies, D-glucuronic acid was reduced to D-glucitol, which was characterized as the hexaacetate.98 As uronic acid residues in a polysaccharide may be reduced relatively easily,465,466 determination as the alditol provides an alternative method of analysis.461,468 This procedure is most valuable when different uronic acids are present in... 

In concentrated sulfuric acid, D-glucuronic acid is dehydrated more slowly than either its 4-O-methyl derivative or D-glucose, probably because of the stability of its lactone. All hexuronic acids, however, eventually produce the same characteristic absorbance that corresponds roughly to a composite of 5-formyl-2-furoic acid, 2-furaldehyde, and reductic acid. It is interesting that a thin-layer chromatographic examination of the reaction products of D-glucuronic acid with 89% sulfuric acid at 70° revealed 5-formyl-2-furoic acid as a major product, but no evidence was obtained for the presence of reductic acid. This result is in distinct contrast to the products obtained in dilute acid solutions, in which 5-formyl-2-furoic acid is produced in very low yield, whereas reductic acid is formed in yields in excess of 10%. 

D-glucuronic acid. Recently Serchi and Arcangeli20 reported an eighty-eight percent reduction to sirupy glucuronic acid from which D-glucurono-lactone was claimed to have been crystallized in nearly quantitative yield. 

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