2022 Fiscal Year Final Research Report
Development of a domino-type asymmetric synthesis process triggered by biocatalytic functional group transformations
| Project/Area Number |
20K05870
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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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| Review Section |
Basic Section 38040:Bioorganic chemistry-related
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| Research Institution | Meisei University |
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Principal Investigator |
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| Project Period (FY) |
2020-04-01 – 2023-03-31
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| Keywords | 生体触媒 / 不斉異性化 / プロトン移動 / エナンチオ面選択性 / 酸化 / 環化 / ドミノ反応 |
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| Outline of Final Research Achievements |
The domino-type reactions in which highly reactive intermediates generated by biocatalysts are converted to optically active products with excellent yields and asymmetric yields in an asymmetric reaction field formed by amino acid residues of enzymes, were studied. Specifically, we addressed two issues: remote asymmetric induction triggered by biocatalytic hydrolysis and domino-type oxidation-asymmetric cyclization triggered by biocatalysts. One particularly interesting result was the discovery, in the investigation of synthetic studies on butenolides, that the biocatalytic generation of a highly reactive dienolate of them and subsequent isomerization with proton transfer proceeded enantioface-selectively at the γ-position. Using this reaction, the synthesis of various optically active butenolides was achieved.
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| Free Research Field |
有機化学、酵素化学、応用微生物学
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| Academic Significance and Societal Importance of the Research Achievements |
既存のタンパク質やゲノムのデータベースに捉われず、独自の分子設計に基づく低分子化合物を基質として用いることにより、全く新しい活性を示す酵素を見つけ出すことができる。性質や機能、構造に基づき新しい酵素を体系化することにより、生体触媒としての利用のみならず、生合成系の人為的なデザインに利用でき、天然物を凌ぐ生物活性を示す有用物質の供給につながると期待できる。
基質の適切な分子設計により生物活性天然物の合成に直結する斬新な生体触媒プロセスを開発してその有用性を示せば、多くの有機合成化学者による生体触媒の利用につながり、この分野の発展に大きく寄与することができる。
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