Structural Analysis of Novel Low-Digestible Sucrose Isomers Synthesized from D-Glucose and D-Fructose by Thermal Treatment

J Appl Glycosci (1999). 2017 Feb 20;64(1):15-19. doi: 10.5458/jag.jag.JAG-2016_011. eCollection 2017.

Abstract

The synthesis of the saccharide β-D-fructopyranosyl-(2→6)-D-glucopyranose, which was isolated from Super Ohtaka®, has recently been reported. During the synthesis of this saccharide, the formation of two novel saccharides from D-glucose and D-fructose was observed. The present study aimed to confirm the structures of the two disaccharides synthesized from D-glucose and D-fructose by thermal treatment. Furthermore, various properties of the saccharides were investigated. Both saccharides were isolated from the reaction mixture by carbon-Celite column chromatography and an HPLC system and were determined to be novel sucrose-isomers, β-D-fructopyranosyl-(2↔1)-β-D-glucopyranoside (1) and β-D-fructofuranosyl-(2↔1)-β-D-glucopyranoside (2), by MALDI-TOF MS and NMR analyses. Both saccharides showed low digestibility in vitro, and the sweetness of saccharide 2 was 0.45 times that of sucrose.

Keywords: disaccharide; fermented beverage of plant extract; sucrose-isomer; thermal treatment.