Efficient Synthesis of Unnatural Amino Acids Based on Activation of Hydroxyl Groups
| Project/Area Number |
16K08167
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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 |
Chemical pharmacy
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| Research Institution | Nagasaki University |
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Principal Investigator |
ONOMURA Osamu 長崎大学, 医歯薬学総合研究科(薬学系), 教授 (60304961)
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
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| Keywords | 非天然アミノ酸 / 不斉非対称化 / 光学分割 / 銅触媒 / 不斉酸化 / 水酸基活性化 / 不斉スルホニル化 / セリノール / 二置換アミノ酸 / グリセリン / グリセリン酸 / 合成化学 |
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| Outline of Final Research Achievements |
Based on activation of hydroxyl group which caused by chelation of diols with chiral copper catalyst,we have developed 3 methods to prepare unnatural amino acid derivatives with high optical purities: (1) Oxidative asymmetric desymmetrization of alpha-substituted serinols to prepare alpha-substituted serine derivatives, (2) Enantioselective protections for 3-hydroxyl groups of trisethanolamine in asymmetric desymmetrization manner , (3) Sulfonylative asymmetric desymmetrization of alpha-substituted serinols to prepare optically active quaternary-substituted aziridine derivatives and its application to prepare unnatural amino acid derivatives.
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| Academic Significance and Societal Importance of the Research Achievements |
ポストゲノム時代に突入した今日の新薬開発において、擬似ペプチド医薬品の開発が精力的に進められている。擬似ペプチドを構成する基本要素である非天然型アミノ酸やその誘導体は、天然ペプチド中のアミノ酸と異なり自然界から抽出や発酵法による生産が難しく、人工的に光学純度良く合成する必要がある。そのような観点から、多様な非天然型アミノ酸及びその誘導体を簡単に合成できる触媒的反応の開発は価値が高い。
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Report
(4 results)
Research Products
(32 results)
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[Presentation] Highly Eficient Oxidation of Cyclohexane to Adipic Acid2016
Author(s)
Osamu Onomura, Yohei Matsumoto, Masami Kuriyama
Organizer
The 12th international Symposium on Organic Reactions and The 6th German-Japanese Symposium on Electrosynthesis
Place of Presentation
京都テルサ（京都府・京都市）
Year and Date
2016-04-22
Related Report
Int'l Joint Research / Invited
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