Enzymic deacylation of esterified mono- and disaccharides. 3. The location of acetylated positions in partially acetylated sugars

Abstract

The nitrate ester, formed by reaction with fuming nitric acid in acetic anhydride at 0 'C, was suitable to block free hydroxyl groups in partially acetylated sugars without acetyl migration. This allowed the acetylated positions in partially acetylated mono-and disaccharides to be located by the reaction sequence: nitration, deacetylation, methylation, de-nitration, disaccharide hydrolysis and methyl glycosylation (initial product identification by paper partition chromatography), acetylation, and analysis of the products by gas-liquid partition chromatography. D-Glucose, penta-0-acetyl-D-glucopyranose, and 2,3-di-0-acetyl-P-D-glucopyranose were used as test con~pounds in the evaluation of this scheme.