
TY  - JOUR
A1  - Manley-Harris, M 
A1  - Moody, W 
A1  - Richards, GN 
T1  - Mechanisms of alkaline degradation of sucrose. Relative rates of alkaline degradation of some sucrose derivatives
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1980
VL  - 33
IS  - 5
SP  - 1041
EP  - 1047
KW  - 
UR  - https://doi.org/10.1071/CH9801041 
N2  - 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. 
ER  -

