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著作: [中尾 允泰]/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/[薬学雑誌]

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EID
342573
EOID
956959
Map
0
LastModified
2019年8月19日(月) 17:48:15
Operator
大家 隆弘
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TRUE
Censor
0
Owner
中尾 允泰
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種別 必須 総説·解説
言語 必須 日本語
招待 推奨
審査 推奨
カテゴリ 推奨 研究
共著種別 推奨
学究種別 推奨
組織 推奨
著者 必須
  1. 中尾 允泰([徳島大学.大学院医歯薬学研究部.薬学域.薬科学部門.創薬科学系.分子創薬化学])
    役割 任意
    貢献度 任意
    学籍番号 推奨
題名 必須

(英) Development of Novel Functional Molecules Based on the Molecular Structure Characteristics of Diketopiperazines

(日) 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

副題 任意
要約 任意

(英) 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/ϖ interactions, based on the electronic effects of para-substituents on the benzyl group in H 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 H 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.

キーワード 推奨
  1. (英) Aldehydes
  2. (英) Catalysis
  3. (英) Chelating Agents
  4. (英) Crystallography, X-Ray
  5. (英) Cyclization
  6. (英) Diketopiperazines
  7. (英) Magnetic Resonance Spectroscopy
  8. (英) Methylation
  9. (英) Microwaves
  10. (英) Molecular Conformation
  11. (英) Oligopeptides
  12. (英) Organic Chemistry Phenomena
  13. (英) Piperazines
  14. (英) Solvents
  15. (英) Spectrometry, Mass, Electrospray Ionization
発行所 推奨
誌名 必須 薬学雑誌([日本薬学会])
(pISSN: 0031-6903, eISSN: 1347-5231)
ISSN 任意 1347-5231
ISSN: 0031-6903 (pISSN: 0031-6903, eISSN: 1347-5231)
Title: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan
Title(ISO): Yakugaku Zasshi
Supplier: 公益社団法人日本薬学会
Publisher: Pharmaceutical Society of Japan
 (NLM Catalog  (Webcat Plus  (Webcat Plus  (医中誌Web  (J-STAGE  (J-STAGE  (J-STAGE  (J-STAGE  (Scopus  (CrossRef (Scopus information is found. [need login])
必須 137
必須 12
必須 1505 1516
都市 任意
年月日 必須 2017年 12月 2日
URL 任意
DOI 任意 10.1248/yakushi.17-00176    (→Scopusで検索)
PMID 任意 29199259    (→Scopusで検索)
NAID 任意
WOS 任意
Scopus 任意 2-s2.0-85037343536
評価値 任意
被引用数 任意
指導教員 推奨
備考 任意
  1. (英) Article.ELocationID: 10.1248/yakushi.17-00176

  2. (英) Article.PublicationTypeList.PublicationType: Journal Article

  3. (英) Article.PublicationTypeList.PublicationType: Review

  4. (英) KeywordList.Keyword: CH/ϖ interaction

  5. (英) KeywordList.Keyword: N-methylation

  6. (英) KeywordList.Keyword: conformation

  7. (英) KeywordList.Keyword: diketopiperazine

  8. (英) KeywordList.Keyword: organocatalyst

  9. (英) KeywordList.Keyword: siderophore