Synthesis of glucose and galactose derivatives containing nitroso (N = O) group

Author: neli sidamonidze
Co-authors: Neli Sidamonidzea, Ramaz Gakhokidzeb Rusudan Vardiashvilib, Maia Nutsubidzeb
Keywords: Key word: carbohydrates, nitroso (N=O) group, condensation
Annotation:

Synthesis of carbohydrate derivatives and studyof their biological activityis an important process for disease prevention. Especially, carbohydrate scontaining nitrosogroup,because theyhavean effectof vasodilator; Theyplay an important role in theprocess of apoptosisandcell proliferation. Also, carbohydrate derivatives containing nitrosogroup participates in the functioningof the immune system and nervous system. The goal of present investigation consist in synthesis of N-glycosilamines. Аs аn initial substance in the given work has been used the products of condensation of D-glucose and D-galactose with p-nitroaniline - β-N-(p-nitrophenyl)-D-glucopyranosilamine (3) and β-N (p-nitrophenyl)-D-galactopyranosilamine (4). Acetylation of the latter with acetic anhydride in the presence of sodium acetate gave β-N-(p-nitrophenyl)-2,3,4,6-tetra-0-acetyl-D-glucopyranosylamine (5) and β-N-(p-nitrophenyl)-2,3,4,6-tetra-0-acetyl-D-galactopyranosyl-amine (6). In the interaction of compounds (5 and 6) with sodium nitrite, the corresponding nitroso derivatives were obtained: β-N-nitroso-N-(p-nitrophenyl)-2,3,4,6-tetra-0-acetyl-D-glucopyranosylamine (7) and β-N-nitroso-N-(p-nitrophenyl)-2,3,4,6-tetra-0-acetyl-D-galactopyranosylamine (8). Reaction proceeds according to the following scheme: