H-Glu(OtBu)-Pro-Phe-Phe-Ala-OH | 170458-76-1

• 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: H-Glu(OtBu)-Pro-Phe-Phe-Ala-OH
• CAS: 170458-76-1
• 化学式: C₃₅H₄₇N₅O₈
• 分子量: 665.787
• InChiKey: SUPIWXDDBPINRO-COCCXFIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.47
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  197.23
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  H-Glu(OtBu)-Pro-Phe-Phe-Ala-OH 、 (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 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以7%的产率得到cyclo<-Pro-Phe-Phe-Ala-Glu(OtBu)->2
  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：

  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 24.0h， 以1.7 g的产率得到H-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