Mechanisms of alkaline degradation of sucrose. Relative rates of alkaline degradation of some sucrose derivatives
Australian Journal of Chemistry
33(5) 1041 - 1047
An earlier study of the relative rates of degradation of several sucrose derivatives has been refined and extended. The results support a novel hypothesis to explain the unusual alkali-lability of sucrose (1). In this hypothesis the first and rate-determining step in the degradation is an SN1cB displacement effected at the C1 anomeric centre of the glucose moiety by an oxyanion derived from the C1' hydroxyl (10), to produce 1-(α-D-glucopyranosyl)fructose (11). The latter is then very rapidly degraded, mainly to lactic acid. The possibility of analogous competing displacements involving the 3' and 6' oxyanions remains for further investigation.
© CSIRO 1980