COMPARATIVE STABILITY OF 1-ALKOXYALKYL α-D-GLUCOSIDES IN THE PRESENCE OF ACID OR α-D-GLUCOSIDASE FROM YEAST

Article abstract of DOI:10.1016/S0008-6215(00)90732-8

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 glucosides compared with aminated ordinary glycosides suggest essential differences in the mechanism of acid-catalysed hydrolysis.