
%0 Journal Article
%A Manley-Harris, M 
%A Moody, W 
%A Richards, GN 
%T Mechanisms of alkaline degradation of sucrose. Relative rates of alkaline degradation of some sucrose derivatives
%J Australian Journal of Chemistry
%D 1980/05/01
%V 33
%N 5
%P 1041-1047
%K 
%R https://doi.org/10.1071/CH9801041
%U https://www.publish.csiro.au/paper/CH9801041 
%X 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-(&#945;-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. 
