CLEAVAGE OF INTERGLYCOSIDIC LINKAGES IN PER(TRIMETHYLSILYL)ATED AND PERMETHYLATED CARBOHYDRATES WITH IODOTRIMETHYLSILANE

Article abstract of DOI:10.1016/0008-6215(83)88138-5

Iodotrimethylsilane in carbon tetrachloride cleaves interglycosidic linkages in per(trimethylsilyl)ated disaccharides to give iodinolysis products that may be readily hydrolyzed to component monosaccharides.The cleavage rate is dependent on the type of interglycosidic linkage, and is in the order (1->4)<(1->2)<(1->3)<(1->6) for derivatives of β-linked glucobioses.This iodinolysis reagent is more reactive toward interglycosidic linkages in permethylated carbohydrates; all of the linkages in the permethylated derivatives examined were completely cleaved, irrespective of linkage type.Iodinolysis with iodotrimethylsilane, followed by treatment of the products with water, offers a rapid and mild method for hydrolysis of permethylated carbohydrates.