Development of a novel sugar linkage and its application to the synthesis of bloactive compounds.
| Project/Area Number |
17590013
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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 |
Chemical pharmacy
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| Research Institution | Teikyo University |
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Principal Investigator |
TAKAHASHI Hideyo Teikyo University, School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (10266348)
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| Co-Investigator(Kenkyū-buntansha) |
NAMME Rie Teikyo University, School of Pharmaceutical Sciences, Research assistant, 薬学部, 助手 (70349257)
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| Project Period (FY) |
2005 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2006: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 2005: ¥1,800,000 (Direct Cost: ¥1,800,000)
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| Keywords | coyolosa / ether-linked sugar / reductive etherification / hypoglycemic activity / oxirane / glycosidation / trehalose / 1C-methyl sugar / Coyolosa / エーテル結合 / アセタール / エーテル |
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| Research Abstract |
In 1997, coyolosa was isolated from the Acrocomia mexicana root. It is worth noting that coyolosa, which is a new carbohydrate connected by a ether-linkage, shows a significant effect on the decreasing blood glucose level. So far, no studies on the sugar linkage by ether-bonding have ever been reported. Thus, we examined a novel synthesis of ether-connected pyranoses. We adopted an acetalization-reduction procedure, which is a convenient method for the preparation of ethers under non-basic conditions. Since a two-step procedure is inconvenient, the one-pot reductive etherification was also investigated. Utilizing the method mentioned above, various ether-connected pyranoses were synthesized. Their SAR studies showed that the mannose-connected pyranose has the hypoglycemic activity as potent as coyolosa, suggesting that the correct structure of coyolosa would be the mannose-connected pyranose rather than the proposed allose-connected one. We next examined a new approach utilizing regioselective ring opening of oxirane to give the rare sugars connected by ether linkage.
A novel synthesis of trehalose analogues by the glycosidation of 1C-methyl sugars is also developed.
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Report
(3 results)
Research Products
(22 results)
