(L-O-Val-L-Val-D-O-Leu-D-Ala)₃ | 1189526-12-2

• 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: (L-O-Val-L-Val-D-O-Leu-D-Ala)₃
• 英文别名: L-O-valine-L-valine-D-O-leucine-D-alanine-L-O-valine-L-valine-D-O-leucine-D-alanine-L-O-valine-L-valine-D-O-leucine-D-alanine；(2R)-2-[[(2R)-2-[(2S)-2-[[(2S)-2-[(2R)-2-[[(2R)-2-[(2S)-2-[[(2S)-2-[(2R)-2-[[(2R)-2-[(2S)-2-[[(2S)-2-hydroxy-3-methylbutanoyl]amino]-3-methylbutanoyl]oxy-4-methylpentanoyl]amino]propanoyl]oxy-3-methylbutanoyl]amino]-3-methylbutanoyl]oxy-4-methylpentanoyl]amino]propanoyl]oxy-3-methylbutanoyl]amino]-3-methylbutanoyl]oxy-4-methylpentanoyl]amino]propanoic acid
• CAS: 1189526-12-2
• 化学式: C₅₇H₉₈N₆O₁₉
• 分子量: 1171.43
• InChiKey: AKOCOTUURHEJAS-UHZBFKKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  82
• 可旋转键数：
  40
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  364
• 氢给体数：
  8
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  (L-O-Val-L-Val-D-O-Leu-D-Ala)₃ 在 4-二甲氨基吡啶 、 间硝基苯甲酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 41.0h， 以73%的产率得到cereulide
  参考文献：
  名称：

  Synthesis of Four Lysine-Linked Cereulide Analogues Showing Ionophoric Activity Towards Potassium Cations as Lead Compounds for Emetic Toxin-Detection by Immunoassays

  摘要：

  描述了一种改进的呕吐毒素cereulide的总体合成及四种赖氨酸连接的cereulide类似物的制备。cereulide类似物是通过用赖氨酸替换cereulide中的一种氨基酸残基制备的。这些cereulide类似物对碱金属离子和无机铵离子表现出离子载体活性，目前正在用于开发针对cereulide的酶联免疫吸附测定法。

  DOI：

  10.1055/s-0029-1216837
• 作为产物：
  描述：

  (R)-2-羟基-4-甲基戊酸 在 吡啶 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢氟酸 、 氢气 、 1-羟基苯并三唑 、 对甲基苯甲酰氯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 生成 (L-O-Val-L-Val-D-O-Leu-D-Ala)₃
  参考文献：
  名称：

  Chemical structure of hydrolysates of cereulide and their time course profile

  摘要：

  Hydrolysates of an emetic toxin cereulide were found in the broth of Bacillus cereus. The ester cleaved depsipeptides of cereulide were synthesized using liquid phase fragment condensation method starting from commercially available amino acids. The chemical structure of hydrolysates was verified tetradepsipeptide L-O-Val-L-Val-D-O-Leu-D-Ala and dodecadepsipeptide (D-O-Leu-D-Ala-L-O-Val-L-Val)(3) using LC-TOFMS. Quantitative analysis of cereulide in the broth revealed production of cereulide in the stationary phase and decomposition in the death phase. The increase in tetradepsipeptide continued after the stationary phase until decomposition occurred.

  DOI：

  10.1016/j.bmcl.2020.127050

文献信息

• Synthesis of Four Lysine-Linked Cereulide Analogues Showing Ionophoric Activity Towards Potassium Cations as Lead Compounds for Emetic Toxin-Detection by Immunoassays
  作者：Minoru Isobe、Arthit Makarasen、Toshio Nishikawa

  DOI：10.1055/s-0029-1216837

  日期：2009.7

  An improved total synthesis of the emetic toxin cereulide and the preparation of four lysine-linked cereulide analogues is described. The cereulide analogues are prepared by replacing one of the amino acid residues in cereulide with lysine. The cereulide analogues demonstrate ionophoric activity towards alkali metal ions and inorganic ammonium ions, and are currently being used to develop an enzyme-linked immunosorbent assay for cereulide.

  描述了一种改进的呕吐毒素cereulide的总体合成及四种赖氨酸连接的cereulide类似物的制备。cereulide类似物是通过用赖氨酸替换cereulide中的一种氨基酸残基制备的。这些cereulide类似物对碱金属离子和无机铵离子表现出离子载体活性，目前正在用于开发针对cereulide的酶联免疫吸附测定法。
• Chemical structure of hydrolysates of cereulide and their time course profile
  作者：Toshihito Naka、Yuka Takaki、Yoshihide Hattori、Hiroshi Takenaka、Yoichiro Ohta、Mitsunori Kirihata、Shinji Tanimori

  DOI：10.1016/j.bmcl.2020.127050

  日期：2020.5

  Hydrolysates of an emetic toxin cereulide were found in the broth of Bacillus cereus. The ester cleaved depsipeptides of cereulide were synthesized using liquid phase fragment condensation method starting from commercially available amino acids. The chemical structure of hydrolysates was verified tetradepsipeptide L-O-Val-L-Val-D-O-Leu-D-Ala and dodecadepsipeptide (D-O-Leu-D-Ala-L-O-Val-L-Val)(3) using LC-TOFMS. Quantitative analysis of cereulide in the broth revealed production of cereulide in the stationary phase and decomposition in the death phase. The increase in tetradepsipeptide continued after the stationary phase until decomposition occurred.