(3S,6R,12S,15S,18S,24S,27S,30S)-24-benzyl-3-[(2S)-butan-2-yl]-12-[(1R)-1-hydroxyethyl]-27-(1H-indol-3-ylmethyl)-9,9-dimethyl-15-(2-methylpropyl)-8-thia-1,4,10,13,16,22,25,28-octazatetracyclo[28.3.0.06,10.018,22]tritriacontane-2,5,11,14,17,23,26,29-octone | 1501965-55-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (3S,6R,12S,15S,18S,24S,27S,30S)-24-benzyl-3-[(2S)-butan-2-yl]-12-[(1R)-1-hydroxyethyl]-27-(1H-indol-3-ylmethyl)-9,9-dimethyl-15-(2-methylpropyl)-8-thia-1,4,10,13,16,22,25,28-octazatetracyclo[28.3.0.06,10.018,22]tritriacontane-2,5,11,14,17,23,26,29-octone
• CAS: 1501965-55-4
• 化学式: C₅₂H₇₁N₉O₉S
• 分子量: 998.257
• InChiKey: BCNADIUZQVZRBA-BDMJUSPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  71
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  268
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  在 三异丙基硅烷 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 生成 (3S,6R,12S,15S,18S,24S,27S,30S)-24-benzyl-3-[(2S)-butan-2-yl]-12-[(1R)-1-hydroxyethyl]-27-(1H-indol-3-ylmethyl)-9,9-dimethyl-15-(2-methylpropyl)-8-thia-1,4,10,13,16,22,25,28-octazatetracyclo[28.3.0.06,10.018,22]tritriacontane-2,5,11,14,17,23,26,29-octone
  参考文献：
  名称：

  Rescuing Biological Activity from Synthetic Phakellistatin 19

  摘要：

  Phakellistatins is one of the families of Pro-rich cyclic peptides whose synthetic counterparts have revealed cytotoxicities that differ greatly from those displayed by their corresponding natural ones. This is also the case of the last member isolated from this family, phakellistatin19, an octacyclopeptide containing three Pro moieties and a high percentage of apolar residues. Exhaustive NMR studies on the synthetic and natural phakellistatin 19 have been performed in order to find a plausible explanation for this intriguing behavior. Moreover, taking advantage of phakellistatin's framework, analogues with different cis/trans geometry at the key prolyl peptide bonds were designed, covering a promising conformational space that could not be reached by the natural peptide. By introduction of proline surrogates (psi(Me,Me)pro residues) in phakellistatin 19, which effectively increases the percentage of cis conformation in the final peptides, this translates into enhanced biological activity, therefore "rescuing" an otherwise inactive cyclopeptide.

  DOI：

  10.1021/jm401520x