| Autor: |
Sano K; Department of Biotechnology, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan., Ishiwata A; RIKEN Cluster for Pioneering Research, Wako 351-0198, Japan., Takamori H; Department of Biotechnology, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan., Kikuma T; Department of Biotechnology, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan., Tanaka K; RIKEN Cluster for Pioneering Research, Wako 351-0198, Japan.; Department of Chemical Science and Engineering, Tokyo Institute of Technology, Tokyo 152-8552, Japan., Ito Y; RIKEN Cluster for Pioneering Research, Wako 351-0198, Japan.; Graduate School of Science, Osaka University, Toyonaka 560-0043, Japan., Takeda Y; Department of Biotechnology, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan. |
| Abstrakt: |
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. |
