N-(17-phosphonooxylinoleoyl)-L-glutamine

• 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: N-(17-phosphonooxylinoleoyl)-L-glutamine
• 英文别名: N-(17-phosphonooxylinoleoyl) glutamine；(2S)-5-amino-5-oxo-2-[[(9Z,12Z)-17-phosphonooxyoctadeca-9,12-dienoyl]amino]pentanoic acid
• 化学式: C₂₃H₄₁N₂O₈P
• 分子量: 504.561
• InChiKey: HAVPOGYPYPIKBB-YHIZTDPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  21
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  176
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  L-谷氨酰胺 在 三甲基溴硅烷 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.08h， 生成 N-(17-phosphonooxylinoleoyl)-L-glutamine
  参考文献：
  名称：

  N-(17-Phosphonooxylinolenoyl)glutamine and N-(17-phosphonooxylinoleoyl)glutamine from Insect Gut:  The First Backbone-Phosphorylated Fatty Acid Derivatives in Nature

  摘要：

  N-(17-Phosphonooxylinolenoyl)glutamine (1) and N-(17-phosphonooxylinoleoyl)glutamine (2) were isolated from the regurgitate of Spodoptora exigua and identified as the first natural alkyl chain-phosphorylated fatty acid derivatives. The compounds were characterized by HPLC-MS/MS and the assigned structures confirmed by synthesis via a dissymmetric bis-Wittig approach as the key reaction. Rearing of the larvae on a diet enriched with inorganic phosphate increased the amount of the phosphorylated N-acyl glutamines in the regurgitate.

  DOI：

  10.1021/jo035382g