Carbohydrate Research p. 73 - 82 (1981)
Update date:2022-08-16
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Aalmo, Kjell M.
Painter, Terence J.
For oxidation in aqueous sodium metaperiodate at 20 deg C, rate coefficients describing the decay of intact glycoside (kG) and the consumption of periodate (kP) were measured for the methyl α- and β-glycopyranosides of D-glucose, D-galactose, D-mannose, D-xylose, and D-(or L-)arabinose, and for methyl α-L-rhamnopyranoside.For glycosides containing a cis-1,2-diol group, kG was four to sixteen times large than for those containing only trans-1,2-diol groups.For anomeric pairs, (kG)α/(kG)β varied from 0.6 to 1.7.The kinetics showed that the singly oxidised intermediates existed partly in an unreactive form, which was inferred to be a cyclic hemiacetal.For hexopyranosides, but not pentopyranosides, the stabilities of the hemiacetals, as indicated by the limiting values of kP, were much greater with α than with β anomers.From a consideration of possible structures and conformations of the hemiacetals, it was inferred that this result was a manifestation of the anomeric effect.
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