| Project/Area Number |
26560443
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical biology
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| Research Institution | Tokyo Medical and Dental University |
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Principal Investigator |
Hosoya Takamitsu 東京医科歯科大学, 生体材料工学研究所, 教授 (60273124)
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| Project Period (FY) |
2014-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | ケミカルバイオロジー / 有機合成化学 / アジド / ピラジン / セレンテラジン / 化学プローブ / 生物発光 / イメージング / ルシフェリン |
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| Outline of Final Research Achievements |
We aimed to develop a new method that is capable of detecting hydrogen sulfide with a novel coelenterazine (CTZ)-type probe. To achieve this purpose, we conducted following studies regarding the synthesis of CTZ-related compounds and reactivities of azide molecules. (1) A novel synthetic method for v-coelenterazine (v-CTZ), which is a vinylene-bridged analog of native CTZ with a large red-shifted luminescence property, has been developed. The synthesis was achieved in a concise way through the use of three sequential cross-coupling reactions and ring-closing metathesis (RCM). (2) We have found that four different substituents can be introduced into pyrazine via four palladium-catalyzed regioselective cross-coupling reactions, using trihalogenated aminopyrazine as the starting material. (3) We have revisited the reduction of azides using a variety of phosphines and achieved a selective reduction of an aromatic azido group under mild conditions.
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