Z-Glu(OtBu)-Pro-Phe-Phe-Ala-OH | 170458-79-4

• 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
• 英文名称: Z-Glu(OtBu)-Pro-Phe-Phe-Ala-OH
• CAS: 170458-79-4
• 化学式: C₄₃H₅₃N₅O₁₀
• 分子量: 799.921
• InChiKey: AWMNBACVKNVLLO-HCJIVJCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  58.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  209.54
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Z-Glu(OtBu)-Pro-Phe-Phe-Ala-OH 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.17h， 生成 (S)-4-Amino-5-((S)-2-{(S)-1-[(S)-1-((S)-2-isobutoxycarbonyloxy-1-methyl-2-oxo-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-pyrrolidin-1-yl)-5-oxo-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  A potent cyclolinopeptide A analog: Solid state and solution conformation of cyclo[Pro-Phe-Phe-Ala-Glu(OtBu)]2.

  摘要：

  The conformational analysis of cyclo[Pro-Phe-Phe-Ala-Glu(OtBu)](2), in the solid state and in solution, has been carried out by X-ray diffraction and NMR spectroscopy. The structure of the orthorhombic form obtained from dioxane-water-acetonitrile mixture [a = 9.994(1) Angstrom, b = 21.846(5) Angstrom, c = 37.357(9) Angstrom, space group P2(1)2(1)2(1); Z = 4] shows the presence of four intramolecular NH-CO hydrogen bonds, with formation of two beta turns (one of type I and one of type II) and two C-14 ring structures. All peptide units are trans. The solution structure, as determined by NMR, indicates that, at room temperature, the peptide is conformationally homogeneous; the structure determined is perfectly symmetrical and topologically similar to that found in the solid state. The cyclodecapeptide exhibits similar biological activity to cyclolinopeptide A.

  DOI：

  10.1021/ja00138a022
• 作为产物：
  描述：

  (S)-4-Benzyloxycarbonylamino-5-isobutoxycarbonyloxy-5-oxo-pentanoic acid tert-butyl ester 在 N-甲基吗啉 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 Z-Glu(OtBu)-Pro-Phe-Phe-Ala-OH
  参考文献：
  名称：

  A potent cyclolinopeptide A analog: Solid state and solution conformation of cyclo[Pro-Phe-Phe-Ala-Glu(OtBu)]2.

  摘要：

  The conformational analysis of cyclo[Pro-Phe-Phe-Ala-Glu(OtBu)](2), in the solid state and in solution, has been carried out by X-ray diffraction and NMR spectroscopy. The structure of the orthorhombic form obtained from dioxane-water-acetonitrile mixture [a = 9.994(1) Angstrom, b = 21.846(5) Angstrom, c = 37.357(9) Angstrom, space group P2(1)2(1)2(1); Z = 4] shows the presence of four intramolecular NH-CO hydrogen bonds, with formation of two beta turns (one of type I and one of type II) and two C-14 ring structures. All peptide units are trans. The solution structure, as determined by NMR, indicates that, at room temperature, the peptide is conformationally homogeneous; the structure determined is perfectly symmetrical and topologically similar to that found in the solid state. The cyclodecapeptide exhibits similar biological activity to cyclolinopeptide A.

  DOI：

  10.1021/ja00138a022