2022 Fiscal Year Final Research Report
Synthesis of cyclic phosphonic anhydride and its applications
| Project/Area Number |
20K06971
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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 47010:Pharmaceutical chemistry and drug development sciences-related
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| Research Institution | Kitasato 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 | 環状リン酸無水物 |
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| Outline of Final Research Achievements |
In vivo, phosphoric acid anhydride, as represented by adenosine triphosphate, has excellent chemical reactivity and functions as a reactant for the phosphorylation of hydroxy and carboxy groups. In particular, when a hydroxy group at anomeric position of a sugar or a carboxy group of an amino acid is phosphorylated, these functional groups are converted to leaving groups, promoting the formation of glycosidic and peptidic linkages. Using such in vivo reactions as a model, we have synthesized the three cyclic phosphoric anhydrides and applied them to catalytic amidation reactions involving dehydration of carboxylic acid and amine to obtain the desired amide.
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| Free Research Field |
有機化学
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| Academic Significance and Societal Importance of the Research Achievements |
生体内において糖鎖やペプチドは極めて重要な働きをしており，その生理機能の解明や医薬品開発への応用のためには，これらの量的供給を可能とする実用的な方法論の開発が望まれている。本研究では，生体内におけるアミド化反応やグリコシル化反応をモデルとして，三次元構造が固定された環状リン酸無水物の合成と脱水反応を伴う触媒的アミド化反応への適用を目指し研究を行った。その結果，我々のデザインした環状リン酸無水物がカルボン酸とアミンとのアミド化反応を促すことが明らかになった。現状において触媒効率は低いものの，環状リン酸無水物が分子触媒として機能する可能性を示すことができた。
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