Comparative stability of 1-alkoxyalkyl α- d-glucosides in the presence of acid or α- d-glucosidase from yeast

The aminated 1-alkoxyalkyl glycosides [( S)-2-amino-1-methoxyethyl] 6- amino-6-deoxy-α- d-glucopyranoside ( 3) and [( R,S)-1-ethoxyethyl] 6-amino-6- deoxy-α- d-glucopyranoside ( 4) have been synthesised and characterised. These compounds as well as [( R)-2-amino-1-methoxyethyl] α- d-glucopyranoside ( 1) prepared earlier are resistant against α- d-glucosidase (maltase, α- d-glucoside glucohydrolase, E.C. 3.2.1.20) from yeast, yet undergo hydrolysis under relatively mild acidic conditions. The kinetic parameters of the interaction with α- d-glucosidase and with acid were determined. The relative rates of acid hydrolysis of aminated 1-alkoxyalkyl glycosides compared with aminated ordinary glycosides suggest essential differences in the mechanism of acid-catalysed hydrolysis.