| Project/Area Number |
17K18148
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Bio-related chemistry
Basic / Social brain science
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| Research Institution | Toho University |
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Principal Investigator |
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| Project Period (FY) |
2017-04-01 – 2020-03-31
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| Project Status |
Completed (Fiscal Year 2019)
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| Budget Amount *help |
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
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| Keywords | バイオテクノロジー / 有機化学 / 脳・神経 / 光化学 / ケミカルバイオロジー / ケージド化合物 |
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| Outline of Final Research Achievements |
In this study, I developed new photolabile protecting groups having a novel photochemical property by introducing olefins to 6-bromo-7-hydroxycoumarin-4-ylmethyl (Bhc) group. Using 8-formyl Bhc-caged acetic acid, which I had developed in previous study, and Wittig reagents, I synthesized a variety of olefin-extended Bhc groups. These olefin-extended Bhc acetic acids had slightly red-shifted absorption maxima around 390 nm compared to normal Bhc acetic acid which has the maximum at 370 nm. They also showed absorption over 450 nm and photolyzed by 450 nm light which never reacted with normal Bhc-caged acetic acid, although their photolysis efficiencies, Φε450, were quite low, within a range of 1.5 to 5.6. These results suggested that olefin extension of 8-formyl Bhc-caged acetic acid is a powerful method to develop new types of photolabile protecting groups with a novel photochemical property.
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| Academic Significance and Societal Importance of the Research Achievements |
ケージド化合物は、光照射により薬や生理活性物質の放出を、任意の場所、任意のタイミングで制御できる化合物である。ケージド化合物に使われる光分解性保護基は、分解させるための光の波長が異なるなど、光化学特性が異なる様々な保護基が存在することが望ましい。本研究では、8位にアルデヒド基を持つBhc基に対し、簡単な化学反応でオレフィンを伸展させることで、新しい光化学特性を持つ光分解性保護基を開発した。その結果、Bhc基とは異なる450 nmの波長で分解できるような、新規の光分解性保護基を多種多様に合成することができ、本研究の方法が新種の光分解性保護基の開発に応用可能なことが示された。
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