E. El Ashry, A. Abdel-Rahman, Mohamed Kattab
Jan 1, 2000
Citations
0
Influential Citations
6
Citations
Journal
Journal of Carbohydrate Chemistry
Abstract
ABSTRACT Methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside (6), or its iodo analogue 7, were subjected to nucleophilic displacement with morpholine to give 8, deacetylation of which gave methyl 6-deoxy-6-(morpholin-4-yl)-α-D-glucopyranoside (3). Similarly, 11, 12 and 21 were prepared. The 6-deoxy-6-iodo derivative 16 was subjected to nucleophilic displacement with morpholine and subsequent acetylation to give 15. Deacetylation of 15 gave 17. The kinetic studies for the inhibition of β-D-glucosidase from sweet almond and using o-nitrophenyl β-D-glucopyranoside as substrate exhibited a K i value for 21 on the same order as 1-deoxynojirimycin whereas for 3, a K i value of lesser order was observed.