(3R,6S,12R,15S,18R,21E,24S)-12-benzyl-6-[(2S)-butan-2-yl]-24-[(E,2R,3S)-3-hydroxy-4-methylhex-4-en-2-yl]-3,10,13,15,21-pentamethyl-18-(2-methylpropyl)-1,19-dioxa-4,7,10,13,16-pentazacyclotetracos-21-ene-2,5,8,11,14,17,20-heptone | 1124235-00-2

• 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: (3R,6S,12R,15S,18R,21E,24S)-12-benzyl-6-[(2S)-butan-2-yl]-24-[(E,2R,3S)-3-hydroxy-4-methylhex-4-en-2-yl]-3,10,13,15,21-pentamethyl-18-(2-methylpropyl)-1,19-dioxa-4,7,10,13,16-pentazacyclotetracos-21-ene-2,5,8,11,14,17,20-heptone
• CAS: 1124235-00-2
• 化学式: C₄₄H₆₇N₅O₁₀
• 分子量: 826.043
• InChiKey: GNRFSBPOFSPDNV-UZWZGVIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  59
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3R,6S,12R,15S,18R,21E,24S)-12-benzyl-6-[(2S)-butan-2-yl]-24-[(E,2R,3S)-3-hydroxy-4-methylhex-4-en-2-yl]-3,10,13,15,21-pentamethyl-18-(2-methylpropyl)-1,19-dioxa-4,7,10,13,16-pentazacyclotetracos-21-ene-2,5,8,11,14,17,20-heptone 以 二氯甲烷-D2 为溶剂， 反应 121.0h， 生成 kulokekahilide-2
  参考文献：
  名称：

  Intramolecular ester exchange of potent cytotoxic kulokekahilide-2

  摘要：

  Kulokekahilide-2 is a 26-membered cyclic depsipeptide that exhibits potent cytotoxicity against HeLa and P388 cells with IC50 values of 3.2 and 16 ng/mL, respectively. We have achieved a total synthesis of natural kulokekahilide-2, the NMR spectra of which showed complex signals because of trans and cis conformers at the amide bond. Besides, the spectra revealed that a mixture of 26- and 24-membered cyclic depsipeptides had been produced due to intramolecular ester exchange. The isolated 24-membered compound was transformed into the 26-membered compound over a period of several days. The two isomers have been shown to be in equilibrium and to display almost the same cytotoxicity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.018

文献信息

• Intramolecular ester exchange of potent cytotoxic kulokekahilide-2
  作者：Masahiro Umehara、Yuuki Takada、Yoichi Nakao、Junji Kimura

  DOI：10.1016/j.tetlet.2008.12.018

  日期：2009.2

  Kulokekahilide-2 is a 26-membered cyclic depsipeptide that exhibits potent cytotoxicity against HeLa and P388 cells with IC50 values of 3.2 and 16 ng/mL, respectively. We have achieved a total synthesis of natural kulokekahilide-2, the NMR spectra of which showed complex signals because of trans and cis conformers at the amide bond. Besides, the spectra revealed that a mixture of 26- and 24-membered cyclic depsipeptides had been produced due to intramolecular ester exchange. The isolated 24-membered compound was transformed into the 26-membered compound over a period of several days. The two isomers have been shown to be in equilibrium and to display almost the same cytotoxicity. (C) 2008 Elsevier Ltd. All rights reserved.