Catalytic Chemoselective introduction of Unprotected-Amino group for the Synthesis of alpha-Amino Acids
| Project/Area Number |
15K14930
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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 pharmacy
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| Research Institution | Kyushu University |
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Principal Investigator |
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| Co-Investigator(Kenkyū-buntansha) |
矢崎 亮 九州大学, 薬学研究院, 助教 (70635812)
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| Project Period (FY) |
2015-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2016: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
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| Keywords | 有機化学 / 非天然アミノ酸 / 化学選択性 / アミノ化 / ナイトレノイド / 銅触媒 / 非天然αアミノ酸 |
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| Outline of Final Research Achievements |
In order to synthesize α-amino acid derivatives directly from carboxylic acid equivalents, we developed a first general catalytic α-amination of carboxylic acid oxidation state pronucleophile.
We focused on the bidentate coordinative acylpyrazole and iminoiodinane for the simultaneous activation of both the nucleophile and the electrophile. The bidentate coordination mode enabled chemoselective enolization over readily enolizable ketones and much more acidic nitroalkyl functionality. This is the first catalytic chemoselective deprotonative activation method of a carboxylic acid oxidation state pronucleophile over a highly acidic nitroalkyl functionality. In addition, the present catalysis could be applicable to late-stage α-amination of complex molecules. Mechanistic studies revealed that highly reactive copper nitrenoid species with a radical character was crucial for obtaining the product in high yield.
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Report
(3 results)
Research Products
(42 results)
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[Journal Article] A novel anti-microtubule agent with carbazole and benzohydrazide structures suppresses tumor cell growth in vivo2015
Author(s)
M. Ohira, Y. Iwasaki, C. Tanaka, M. Kuroki, N. Matsuo, T. Kitamura, M. Yukuhiro, H. Morimoto, N. Pang, B. Liu, T. Kiyono, M. Amemiya, K. Tanaka, K. Yoshida, N. Sugimoto, T. Ohshima, M. Fujita
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Journal Title
Biochimica et Biophysica Acta (BBA) - General Subjects
Volume: 1850
Issue: 9
Pages: 1676-1684
DOI
Related Report
Peer Reviewed
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