Synthesis of p-Nitrophenyl 3- and 6-deoxy-a-D-glucopyranosides and Their Specificity to Rice a-Glucosidase

Abstract

3- and 6-Monodeoxy derivatives of ρ-nitrophenyl (PNP) α-D-glucopyranoside (1) were prepared from methyl α-D-glucopyranoside and confirmed to retain 4C1 chair conformations in D2O by 1H-NMR. Rice α-glucosidase did not hydrolyze the 3-, 4- and 6-deoxy derivatives of 1, but revealed high hydrolitic activity against the 2-deoxy derivative of 1.