Preparation and reactivity of a novel disaccharide, glucosyl 1,5-anhydro-d-fructose (1,5-anhydro-3-O-α-glucopyranosyl-d-fructose) Original Research Article

A novel disaccharide, glucosyl 1,5-anhydro-d-fructose (1,5-anhydro-3-O-α-glucopyranosyl-d-fructose, GAF) was enzymatically prepared from 1,5-anhydro-d-fructose (1,5-AF) and cyclomaltoheptaose (β-cyclodextrin). Cyclodextrin glucanotransferase transferred various sizes of maltooligosaccharide to 1,5-AF. Glucoamylase digested the maltooligosyl chain of the products to a glucosyl residue giving a final product, GAF. An NMR analysis of GAF elucidated that the glucose residue was linked to C-3 of the 1,5-AF residue with an ether linkage. Reactivity on the aminocarbonyl reaction of GAF with bovine serum albumin was lower than that of 1,5-AF, but was higher than that of glucose.