2002 Fiscal Year Final Research Report Summary
A Novel Synthetic Method for Oligosaccharide Using Multi-phase System
| Project/Area Number |
13680680
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioorganic chemistry
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| Research Institution | The Noguchi Institute |
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Principal Investigator |
INAZU Toshiyuki The Noguchi Institute, Researcher, 研究部, 研究員 (70151579)
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| Project Period (FY) |
2001 – 2002
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| Keywords | Synthesis of Oligosaccharide / Fluorous Synthesis / Automatic Synthesizer / Glycosylation Reaction / Fluorous Protective Group / Solid-phase Synthesis / Multi-phase System |
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| Research Abstract |
Oligosaccharide synthesis is very important problem in carbohydrate chemistry. Although solid-phase synthesis of oligosaccharide is expected, it seems to be difficult to realize this methodology. We designed the new methodology, which is based on fluorous technology, as an alternative to solid-phase synthesis. we developed the novel fluorous acyl protective group, the Bfp (bisfluorous chain type propanoyl) group and the Hfb (hexafluorous chain type butanoyl) group. Using these fluorous protective groups we studied a method for the fluorous oligosaccharide synthesis. The use of the Bfp group made it possible to rapidly synthesize the galactose β(1-6) pentamer, which is known as a component part of arabinogalactan-proteins, by minimal column chromatography purification. Further, we found the fluorous synthesis using the Hfb group, as a fluorous support similar to the solid support was effective in the synthesis of oligosaccharide. Each synthetic intermediate was able to be easily purified only by simple fluorous-organic solvent extraction, and monitored by TLC, NMR, and MS.
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Research Products
(15 results)
