Comparative stability of 1-alkoxyalkyl alpha-D-glucosides in the presence of acid or alpha-D-glucosidase from yeast.
The aminated 1-alkoxyalkyl glycosides [(S)-2-amino-1-methoxyethyl] 6-amino-6-deoxy-alpha-D-glucopyranoside (3) and [(R,S)-1-ethoxyethyl] 6-amino-6-deoxy-alpha-D-glucopyranoside (4) have been synthesised and characterised. These compounds as well as [(R)-2-amino-1-methoxyethyl] alpha-D-glucopyranoside (1) prepared earlier are resistant against alpha-D-glucosidase (maltase, alpha-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 alpha-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.
D004355:Drug Stability; D005959:Glucosidases / Q000378:metabolism*; D005960:Glucosides / Q000138:chemical synthesis* / Q000378:metabolism; D006027:Glycosides / Q000138:chemical synthesis*; D006851:Hydrochloric Acid; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D012441:Saccharomyces cerevisiae / Q000201:enzymology*; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000378:metabolism*
D005960:Glucosides; D006027:Glycosides; D005959:Glucosidases; D000520:alpha-Glucosidases; D006851:Hydrochloric Acid