A synthetic methodology for selective substitution of inositol without protection and its use for preparation of useful functional materials
| Project/Area Number |
23510257
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Living organism molecular science
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| Research Institution | Ehime University |
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Principal Investigator |
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| Project Period (FY) |
2011 – 2013
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2013: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | イノシトール / バイオマス / 選択的置換反応 / 光学活性 / 塩化リチウム / ジメチルアセトアミド / 酵素反応 / アルコールの活性化 / 置換反応 / 高分子 / LiCl / DMA / 無保護 / 有機合成 / 界面活性剤 / アシル化 |
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| Research Abstract |
Myo-inositol is a promising material as a biomass. To realize this subject, a regioselective substitution on a desired OH group among six ones in inositol should be developed. It has been the most difficult problem, but we have found that dissolution of inositol in LiCl-dimethylacetamide or dimethylsulfoxide successfully promotes a substitution reaction to yield a regioselective 1,3-di-O- or 1-O-substitution product respectively depending on a amount of an electrophile. Desymmetrization of 1,3-diacetyl-myo-inositol by lipase produced monoacetate in a good yield with high optical purity (96% ee).
These fundamental research results directed us to design and synthesize a candidate of a surfactant and a monomer for a functional polymer, aiming at the use of myo-inositol as a biomass.
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Report
(4 results)
Research Products
(22 results)
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[Journal Article] Effects of 1,3-di-O-substituted-myo-inosiotl derivatives on the antiproliferation and caspase-3 activity of HCT-116 and HL-60 cells2014
Author(s)
Noriyuki Hatae, Satoe Yamauchi, Takafumi Saeki, Ichiro Suzuki, Tominari Choshi, Satoshi Hibino, Chiaki Okada, Minoru Hayashi, Yutaka Watanbe, Eiko Toyota
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Journal Title
Chemical Biology Letters
Volume: 1(2)
Pages: 40-43
URL
Related Report
Peer Reviewed
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