Canadian Journal of Chemistry · 1959 · 19 citations · 11 references
Life SciencesBiochemistryChemistryCarbohydrate BiochemistryCarbohydrate ChemistryRedox BiochemistryCarbohydrate MetabolismGlycan BiosynthesisGlycan DegradationGlycan StructureGlycosidic Bond HydrolysisMonosaccharide StereochemistryCleavageControlled DegradationDegradationGlycofuranose StereochemistryGlycofuranose StructureGlycopyranose StructureOxidationSelective Oxidation
Lead tetraacetate in acetic acid is reduced at an unusually rapid rate by sucrose, due to a vigorous preferential cleavage of the 3,4-glycol group in the D-fructofuranosyl moiety. By contrast, periodate attacks the D-glucopyranosyl unit more readily. These marked variations are exhibited also in the same solvent and, therefore, appear to be related to the characteristics of the oxidants themselves. The mechanism of the action of lead tetraacetate is discussed with reference to the stereochemistry of the D-fructofuranose unit. Selective oxidation provides a chemical method for controlled degradation of the sucrose molecule and affords products in which either the D-fructose or the D-glucose residue is modified.
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