Studies on development of novel asymmetric organocatalysts and oligonucleotide-recognition probes based on natural alkaloid
| Project/Area Number |
17K19474
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| Research Category |
Grant-in-Aid for Challenging Research (Exploratory)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Pharmaceutical Sciences and related fields
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| Research Institution | Chiba University |
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Principal Investigator |
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| Project Period (FY) |
2017-06-30 – 2020-03-31
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| Project Status |
Completed (Fiscal Year 2019)
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| Budget Amount *help |
¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2019: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2017: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | アルカロイド / 機能性分子 / 不斉有機触媒 / 分子認識 / 有機不斉触媒 |
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| Outline of Final Research Achievements |
We have found for the first time that the plant alkaloid, calycanthine, functions as an asymmetric organocatalyst. Thus, in the Michael addition reaction of the oxindole derivative with nitroethene, when 20 mol% of calycanthine or a derivative having a substituent introduced on its benzene ring was used, an optically active substance was obtained with a maximum enantiomeric excess of 41%. Furthermore, it has been suggested that the introduction of a secondary amino group on the benzene ring of calycanthine is indispensable to enhance the molecular recognition ability of nucleobases and calycanthines.
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| Academic Significance and Societal Importance of the Research Achievements |
天然物由来の不斉有機触媒として代表的なもの（成功例）は、シンコナアルカロイド類とスパルテインのみであった。今回の研究により、大量かつ容易に入手可能であるにもかかわらず有効利用されてこなかった天然植物アルカロイドのカリカンチンが、有機不斉触媒として機能することを明らかにすることができた。さらに、カリカンチンの特定部位の分子修飾により、本アルカロイドの不斉有機触媒および特定分子認識プローブとしての可能性を引き出すことで、今後の研究を展開するための方向性を示した。
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Report
(4 results)
Research Products
(5 results)
