| 656248-73-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• CAS: 656248-73-6
• 化学式: C₃₃H₄₂N₂O₇
• 分子量: 578.706
• InChiKey: RQZIDXIMCPZKNF-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  42.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  123.19
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 palladium on activated charcoal 盐酸 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 56.17h， 生成 methyl (2S)-5-[[(2S)-5-[[(2S)-4-methyl-2-[[2-(6-octyl-1,3,5,7-tetraoxopyrrolo[3,4-f]isoindol-2-yl)acetyl]amino]pentanoyl]amino]-2-[[2-(5-octoxynaphthalen-1-yl)oxyacetyl]amino]pentanoyl]amino]-2-[[2-(5-octoxynaphthalen-1-yl)oxyacetyl]amino]pentanoate
  参考文献：
  名称：

  Zipper-Featured δ-Peptide Foldamers Driven by Donor−Acceptor Interaction. Design, Synthesis, and Characterization

  摘要：

  Donor-acceptor interaction between electron-rich 1,5-dioxynaphthalene (DAN) and electron-deficient pyromellitic diimide (PDI) has been utilized to induce the formation of a new kind of zipper-featured delta-peptide foldamers. Seven L-ornithine-based delta-peptides 1a-g, in which one to three DNA and PDI units are incorporated to the two ends of the peptide backbones, respectively, have been designed and prepared by the standard liquid-phase synthetic method. H-1 NMR, LTV-vis, and fluorescent quenching studies reveal that all the delta-peptides adopt folding conformations in nonpolar chloroform and polar DMF as a result of intramolecular donor-acceptor interaction between the DAN and PDI units. The folding states become more compact for the peptide skeletons possessing more donor-acceptor interacting sites. Variable-temperature LTV-vis experiments indicate that, although the folding is a dynamic process, the folding state can remain even at 150degreesC in DMF. Circular dichroism (CD) investigations reveal that the new generation of delta-peptides have similar folding patterns. A zipper-featured folding motif has been proposed for the new generation of delta-peptide foldamers. Molecular modeling has generated two most stable folding states for the longest 6-peptide 1g, with an energy difference of 26.80 kcal/mol.

  DOI：

  10.1021/jo035149i
• 作为产物：
  描述：

  (S)-5-Benzyloxycarbonylamino-2-[2-(5-octyloxy-naphthalen-1-yloxy)-acetylamino]-pentanoic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以2.30 g的产率得到
  参考文献：
  名称：

  Zipper-Featured δ-Peptide Foldamers Driven by Donor−Acceptor Interaction. Design, Synthesis, and Characterization

  摘要：

  Donor-acceptor interaction between electron-rich 1,5-dioxynaphthalene (DAN) and electron-deficient pyromellitic diimide (PDI) has been utilized to induce the formation of a new kind of zipper-featured delta-peptide foldamers. Seven L-ornithine-based delta-peptides 1a-g, in which one to three DNA and PDI units are incorporated to the two ends of the peptide backbones, respectively, have been designed and prepared by the standard liquid-phase synthetic method. H-1 NMR, LTV-vis, and fluorescent quenching studies reveal that all the delta-peptides adopt folding conformations in nonpolar chloroform and polar DMF as a result of intramolecular donor-acceptor interaction between the DAN and PDI units. The folding states become more compact for the peptide skeletons possessing more donor-acceptor interacting sites. Variable-temperature LTV-vis experiments indicate that, although the folding is a dynamic process, the folding state can remain even at 150degreesC in DMF. Circular dichroism (CD) investigations reveal that the new generation of delta-peptides have similar folding patterns. A zipper-featured folding motif has been proposed for the new generation of delta-peptide foldamers. Molecular modeling has generated two most stable folding states for the longest 6-peptide 1g, with an energy difference of 26.80 kcal/mol.

  DOI：

  10.1021/jo035149i