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

The synthesis of the saccharide beta -D-fructopyranosyl-(2 arrow right 6)-D-glucopyranose, which was isolated from Super Ohtaka super( registered ), has recently been reported. During the synthesis of this saccharide, the formation of two novel saccharides from D-glucose and D-fructose was observed....

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Bibliographic Details
Published in:Journal of applied glycoscience : JAG 2017-01, Vol.64 (1), p.15-19
Main Authors: Yamamori, Akira, Takata, Yusuke, Fukushi, Eri, Kawabata, Jun, Okada, Hideki, Kawazoe, Naoki, Ueno, Keiji, Onodera, Shuichi, Shiomi, Norio
Format: Article
Language:English
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Summary:The synthesis of the saccharide beta -D-fructopyranosyl-(2 arrow right 6)-D-glucopyranose, which was isolated from Super Ohtaka super( registered ), 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, beta -D-fructopyranosyl-(2 reversible reaction 1)- beta -D-glucopyranoside (1) and beta -D-fructofuranosyl-(2 reversible reaction 1)- beta -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.
ISSN:1344-7882
1880-7291
DOI:10.5458/jag.jag.JAG-2016_011