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- Title
Synthesis of Sucrose-Mimicking Disaccharide by Intramolecular Aglycone Delivery.
- Authors
Sano, Kanae; Ishiwata, Akihiro; Takamori, Hiroto; Kikuma, Takashi; Tanaka, Katsunori; Ito, Yukishige; Takeda, Yoichi
- Abstract
Rare sugars are known for their ability to suppress postprandial blood glucose levels. Therefore, oligosaccharides and disaccharides derived from rare sugars could potentially serve as functional sweeteners. A disaccharide [α-d-allopyranosyl-(1→2)-β-d-psicofuranoside] mimicking sucrose was synthesized from rare monosaccharides D-allose and D-psicose. Glycosylation using the intermolecular aglycon delivery (IAD) method was employed to selectively form 1,2-cis α-glycosidic linkages of the allopyranose residues. Moreover, β-selective psicofuranosylation was performed using a psicofuranosyl acceptor with 1,3,4,6-tetra-O-benzoyl groups. This is the first report on the synthesis of non-reducing disaccharides comprising only rare d-sugars by IAD using protected ketose as a unique acceptor; additionally, this approach is expected to be applicable to the synthesis of functional sweeteners.
- Subjects
DISACCHARIDES; BLOOD sugar; SUCROSE; MONOSACCHARIDES; SUGARS; GLYCOSYLATION; INTRAMOLECULAR forces; OLIGOSACCHARIDES
- Publication
Molecules, 2024, Vol 29, Issue 8, p1771
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules29081771