D. Charon, L. Szabó
1975
Citations
0
Influential Citations
4
Citations
Journal
Methods in Enzymology
Abstract
Publisher Summary This chapter describes 3-deoxy-2-ketoaldonic acids. The α -hydroxy group of a 3-deoxyaldonic acid is selectively oxidized by chlorate in the presence of vanadium oxide and phosphoric acid, and the keto acid is isolated by chromatography on cellulose powder. Methyl 3-deoxyheptonate is prepared from commercial 2- deoxy -D-arabino- hexose (2- deoxyglucose). But, the melting point of the crystalline material varies from one preparation to another owing to the presence of varying amounts of epimers (D-gluco and D-manno-) in the sample. The ratio of the epimers does not affect the yield or the quality of the final product. Galactometasaccharinic acid lactone is a mixture of 3-deoxy D-xylo- and D-lyxo-hexonic acid lactones. For the preparation of ammonium 3-deoxy D -threo- hex-2-ulosonate, this lactone (3.2 g) is first hydrolyzed with sodium hydroxide and then treated with sodium chlorate (740 mg), vanadium oxide (120 mg), and phosphoric acid (0.1 ml) as described for the 7-carbon homolog. Detection of 3-deoxyaldulosonic acids on chromatograms and detection of polyhydroxy compounds on paper chromatograms are also discussed.