2002 Fiscal Year Final Research Report Summary
Drug creation involving hybrid type of low molecular weight biomolecules as lead compounds
| Project/Area Number |
12672079
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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 | Kobe Pharmaceutical University |
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Principal Investigator |
NAITO Takeaki Kobe Pharmaceutical University, Professor, 薬学部, 教授 (00068339)
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| Co-Investigator(Kenkyū-buntansha) |
UEDA Masafumi Kobe Pharmaceutical University, Assistant, 薬学部, 助手 (00340935)
MIYATA Okiko Kobe Pharmaceutical University, Associate Professor, 薬学部, 助教授 (90102110)
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| Project Period (FY) |
2000 – 2002
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| Keywords | sugar / amino acid / radical / oxime ether / Dysiherbaine / Wittig rearrangement |
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| Research Abstract |
Research for exploring new lead compounds for new drugs has focused to one component of biological compounds and not to hybrid components so far. We started our project to develop the most efficient and practical synthetic method for biological hybrid compounds which consist of amino acids, sugars, and nucleic bases.
New synthetic method for amino acids and the related peptides has been developed via the route involving radical addition-cyclization of oxime ethers connected with olefins. The products were converted smoothly into β-amino acids.
We also investigated construction of sugar parts by the radical reactions of the unprotected natural sugars. Stannyl radical addition-cyclization of oxime ethers connected with the carbonyl group proceeded smoothly to afford cyclic amino alcohols which were converted into aminocyclitols. The radical reaction was found to proceed via the most stable transition state involving minimum 1, 3-allylic strain.
Formal synthesis of Dysiherbine was completed via two key reactions which are 1, 2-Wittig rearrangement and asymmetric hydroxylation respectively.
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