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ジケトピペラジンの分子構造特性を基盤とする機能性分子の創製
https://tokushima-u.repo.nii.ac.jp/records/2007069
https://tokushima-u.repo.nii.ac.jp/records/20070692b56e3b5-8c82-4c03-8412-2c63116e05be
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
yakushi_137_12_1505.pdf (1.03 MB)
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| Item type | 文献 / Documents(1) | |||||||||||
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| 公開日 | 2020-01-10 | |||||||||||
| アクセス権 | ||||||||||||
| アクセス権 | open access | |||||||||||
| 資源タイプ | ||||||||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||||||||
| 資源タイプ | journal article | |||||||||||
| 出版社版DOI | ||||||||||||
| 識別子タイプ | DOI | |||||||||||
| 関連識別子 | https://doi.org/10.1248/yakushi.17-00176 | |||||||||||
| 言語 | ja | |||||||||||
| 関連名称 | 10.1248/yakushi.17-00176 | |||||||||||
| 出版タイプ | ||||||||||||
| 出版タイプ | VoR | |||||||||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||||||||
| タイトル | ||||||||||||
| タイトル | ジケトピペラジンの分子構造特性を基盤とする機能性分子の創製 | |||||||||||
| 言語 | ja | |||||||||||
| タイトル別表記 | ||||||||||||
| その他のタイトル | Development of Novel Functional Molecules Based on the Molecular Structure Characteristics of Diketopiperazines | |||||||||||
| 言語 | en | |||||||||||
| 著者 |
中尾, 允泰
× 中尾, 允泰
WEKO
379
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| 抄録 | ||||||||||||
| 内容記述タイプ | Abstract | |||||||||||
| 内容記述 | This article focuses on our investigation of the molecular structure characteristics of diketopiperazines (DKPs), and application of these findings to the development of novel functional molecules. DKPs bearing a benzyl moiety are known to adopt a folded conformation, in which the benzyl moiety is folded over the DKP ring. In order to investigate the driving force behind the folded conformation, we synthesized DKPs bearing a benzyl moiety with different para-substituents, and demonstrated that the folded conformation likely arose from intramolecular CH/p interactions, based on the electronic effects of para-substituents on the benzyl group in 1H NMR spectroscopy. On the other hand, N4-methylation of DKPs bearing a benzyl moiety was found to change their folded conformation to an extended conformation, based on single crystal X-ray crystallography and 1H NMR spectroscopy analysis. Next, we attempted to synthesize both hydroxamate-type siderophores containing the DKP ring: rhodotorulic acid and erythrochelin. Facile synthesis of rhodotorulic acid and its N,N′-dimethylated derivative was achieved by microwave-assisted cyclization of the corresponding dipeptide precursors. Interestingly, N,N′-dimethylated rhodotorulic acid was found to be more soluble in various organic solvents than rhodotorulic acid. Moreover, erythrochelin was synthesized for the first time, and its metal-chelating ability with not only Fe(III) but also Mg(II) was confirmed based on electrospray ionization mass spectrometry (ESI-MS) analysis. Finally, we synthesized DKPs bearing a primary amino group, and found that they could catalyze the asymmetric aldol reaction between hydroxyacetone and p-nitrobenzaldehyde. | |||||||||||
| 言語 | en | |||||||||||
| キーワード | ||||||||||||
| 言語 | en | |||||||||||
| 主題Scheme | Other | |||||||||||
| 主題 | diketopiperazine | |||||||||||
| キーワード | ||||||||||||
| 言語 | en | |||||||||||
| 主題Scheme | Other | |||||||||||
| 主題 | conformation | |||||||||||
| キーワード | ||||||||||||
| 言語 | en | |||||||||||
| 主題Scheme | Other | |||||||||||
| 主題 | CH/p interaction | |||||||||||
| キーワード | ||||||||||||
| 言語 | en | |||||||||||
| 主題Scheme | Other | |||||||||||
| 主題 | N-methylation | |||||||||||
| キーワード | ||||||||||||
| 言語 | en | |||||||||||
| 主題Scheme | Other | |||||||||||
| 主題 | siderophore | |||||||||||
| キーワード | ||||||||||||
| 言語 | en | |||||||||||
| 主題Scheme | Other | |||||||||||
| 主題 | organocatalyst | |||||||||||
| 書誌情報 |
ja : YAKUGAKU ZASSHI(藥學雜誌) en : Journal of the Pharmaceutical Society of Japan 巻 137, 号 12, p. 1505-1516, 発行日 2017-12-01 |
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| 収録物ID | ||||||||||||
| 収録物識別子タイプ | ISSN | |||||||||||
| 収録物識別子 | 13475231 | |||||||||||
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| 収録物識別子タイプ | ISSN | |||||||||||
| 収録物識別子 | 00316903 | |||||||||||
| 収録物ID | ||||||||||||
| 収録物識別子タイプ | NCID | |||||||||||
| 収録物識別子 | AA11696503 | |||||||||||
| 収録物ID | ||||||||||||
| 収録物識別子タイプ | NCID | |||||||||||
| 収録物識別子 | AN00284903 | |||||||||||
| 出版者 | ||||||||||||
| 出版者 | 日本薬学会 | |||||||||||
| 言語 | ja | |||||||||||
| EID | ||||||||||||
| 識別子 | 342573 | |||||||||||
| 識別子タイプ | URI | |||||||||||
| 言語 | ||||||||||||
| 言語 | jpn | |||||||||||
