| Project/Area Number |
17H03024
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Tokyo University of Science |
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Principal Investigator |
Shiina Isamu 東京理科大学, 理学部第一部応用化学科, 教授 (40246690)
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| Co-Investigator(Kenkyū-buntansha) |
中田 健也 島根大学, 学術研究院環境システム科学系, 准教授 (00434019)
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| Project Period (FY) |
2017-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥18,590,000 (Direct Cost: ¥14,300,000、Indirect Cost: ¥4,290,000)
Fiscal Year 2020: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2019: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2018: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2017: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
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| Keywords | 有機合成化学 / 速度論的光学分割 / 動的速度論光学分割 / 全合成 |
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| Outline of Final Research Achievements |
Using our kinetic resolution method of 2-hydroxypropanoic acid esters and the dynamic kinetic resolution method with racemization of the starting materials, we designed a new method for producing optically active esters that surpasses the enzymatic reaction.
In these subjects, we took up racemic secondary alcohols, 2-substituted propanoic esters, and α-amino acids, etc. as substrates for giving optically active substances in high yields using the enantioselective organic synthetic methodologies.
Through the promotion of this subject, we developed an effective method for synthesizing chiral carboxylic acids and related compounds, which are highly versatile and have excellent substrate generality. Furthermore, we accomplished the total synthesis of pharmacologically active compounds which have not been feasible until now.
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| Academic Significance and Societal Importance of the Research Achievements |
我々が独自に開発したKR法およびDKR法を鍵工程として用いることで、学術的ならび社会的に求められている光学活性な特殊アミノ酸ならびに薬理活性化合物の合成手段を確立することに成功した。一つの例として、非天然型アミノ酸であり需要の高い(S)-および(R)-2-アリールグリシン混合物のDKRを試みたところ高エナンチオ選択的に不斉エステル化が進行し、目的とする光学活性エステルを得ることができた。さらに、ラセミ多置換2-アリールプロピオン酸のDKRを利用することで、光学純度の高いドラグマシジンD合成中間体の簡便な供給法を見出すことに成功し、抗腫瘍活性化合物ドラグマシジンDの形式不斉全合成を達成した。
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