Novel click chemistries for chemical biology researches
| Project/Area Number |
24310164
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Partial Multi-year Fund |
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| Section | 一般 |
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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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| Co-Investigator(Renkei-kenkyūsha) |
KII Isao 京都大学, 大学院医学研究科, 特定助教 (80401561)
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| Project Period (FY) |
2012-04-01 – 2015-03-31
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| Project Status |
Completed (Fiscal Year 2014)
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| Budget Amount *help |
¥19,500,000 (Direct Cost: ¥15,000,000、Indirect Cost: ¥4,500,000)
Fiscal Year 2014: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2013: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2012: ¥7,280,000 (Direct Cost: ¥5,600,000、Indirect Cost: ¥1,680,000)
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| Keywords | 化学プローブ / アジド / クリック反応 / アルキン / 化学修飾 / ケミカルバイオロジー / 有機化学 / 機能集積 |
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| Outline of Final Research Achievements |
We have developed efficient methods to conjugate functional molecules by sequential triazole formations. One is a modular synthetic method for bis- and tris-1,2,3-triazoles that include a benzotriazole structure, which was developed on the basis of sequential azide-aryne and azide-alkyne cycloadditions. The key to success was efficient halogen-metal exchange reaction-mediated generation of aryne from ortho-iodoaryl triflates bearing a base-sensitive terminal alkyne moiety, which was achieved using trimethylsilylmethyl Grignard reagent. Another is a transient protection method of cyclooctynes from click reaction with an azide through 1:1 complexation with a cationic copper(I) salt. The application of the method to a cyclooctyne bearing a terminal alkyne enabled the selective copper-catalyzed click conjugation with an azide at the terminal alkyne moiety, which made cyclooctyne derivatives readily accessible.
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Report
(4 results)
Research Products
(67 results)
