PF1171C | 220376-02-3

• 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: PF1171C
• 英文别名: cyclo[2Abz-Pip-N(Me)Leu-Ala-Leu-D-Val]；(11R,14S,17S,20S,23S)-17,21-dimethyl-14,20-bis(2-methylpropyl)-11-propan-2-yl-1,9,12,15,18,21-hexazatricyclo[21.4.0.03,8]heptacosa-3,5,7-triene-2,10,13,16,19,22-hexone
• CAS: 220376-02-3
• 化学式: C₃₄H₅₂N₆O₆
• 分子量: 640.823
• InChiKey: MFLJIVQNUIVQOL-CPFCZLQXSA-N

物化性质

• 沸点：
  944.2±65.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  157
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  H2N-L-Leu-D-Val-Ant-L-Pip-L-MeLeu-L-Ala-OH 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以14.1 mg的产率得到PF1171C
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of PF1171A, C, F, and G, Cyclic Hexapeptides with Insecticidal Activity

  摘要：

  The total synthesis of the cyclic hexapeptides PF1171A, C, F, and G has been achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The synthesis includes a solid-phase peptide coupling with the weakly nucleophilic amino group of an anthranilic acid residue. This was efficiently achieved by in situ generation of an Fmoc-amino acid chloride using triphosgene. The natural products exhibit potent paralytic activities against silkworm larvae, whereas epi-PF1171A and epi-PF1171C, bearing L-Ala instead of D-Ala, were relatively inactive. X-ray crystallographic analysis indicates that intramolecular hydrogen bonds in PF1171 peptides are critical for maintaining their active conformations.

  DOI：

  10.1021/jo500861k

文献信息

• Total Synthesis and Biological Evaluation of PF1171A, C, F, and G, Cyclic Hexapeptides with Insecticidal Activity
  作者：Yuichi Masuda、Ren Tanaka、Kenji Kai、A. Ganesan、Takayuki Doi

  DOI：10.1021/jo500861k

  日期：2014.9.5

  The total synthesis of the cyclic hexapeptides PF1171A, C, F, and G has been achieved by solid-phase synthesis of a linear precursor and solution-phase macrolactamization. The synthesis includes a solid-phase peptide coupling with the weakly nucleophilic amino group of an anthranilic acid residue. This was efficiently achieved by in situ generation of an Fmoc-amino acid chloride using triphosgene. The natural products exhibit potent paralytic activities against silkworm larvae, whereas epi-PF1171A and epi-PF1171C, bearing L-Ala instead of D-Ala, were relatively inactive. X-ray crystallographic analysis indicates that intramolecular hydrogen bonds in PF1171 peptides are critical for maintaining their active conformations.