isopropyl 2-(bis(benzyloxy)phosphoryloxy)-8-hydroxyoctanoate | 1358536-61-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: isopropyl 2-(bis(benzyloxy)phosphoryloxy)-8-hydroxyoctanoate
• CAS: 1358536-61-4
• 化学式: C₂₅H₃₅O₇P
• 分子量: 478.522
• InChiKey: LQERHBNDCDVCSD-UHFFFAOYSA-N

物化性质

• 沸点：
  589.1±50.0 °C(predicted)
• 密度：
  1.168±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  33.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  isopropyl 2-(bis(benzyloxy)phosphoryloxy)-8-hydroxyoctanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  Synthesis and evaluation of tetrahedral intermediate mimic inhibitors of 3-deoxy-d-manno-octulosonate 8-phosphate synthase

  摘要：

  3-Deoxy-o-manno-octulosonate 8-phosphate (KDO8P) synthase catalyses the first committed step in the biosynthesis of 3-deoxy-D-manno-octulosonate (KDO), an important component of the lipopolysaccharide of Gram-negative bacteria. The pathway for KDO biosynthesis has been identified as a potential target of antibacterial drug design. The reaction catalysed by KDO8P synthase is an aldol-like condensation between phosphoenolpyruvate (PEP) and D-arabinose 5-phosphate (ASP) and proceeds through a bis-phosphorylated tetrahedral intermediate. In this study a bisphosphate analogue of the tetrahedral intermediate was synthesised and was found to inhibit the metal-dependent KDO8P synthase from Neisseria meningitidis and the metal-dependent KDO8P synthase from Acidithiobacillus ferrooxidans with inhibition constants in the low micromolar range. Additionally, monophosphorylated inhibitors were synthesised to determine the relative importance of the two phosphate groups of this bisphosphate analogue for enzyme inhibition. The removal of either of these two phosphate groups gave less potent inhibitors for both enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.025
• 作为产物：
  描述：

  isopropyl 8-(tert-butyldimethylsilyloxy)-2-hydroxyoctanoate 在 四氮唑 、 四丁基氟化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 isopropyl 2-(bis(benzyloxy)phosphoryloxy)-8-hydroxyoctanoate
  参考文献：
  名称：

  Synthesis and evaluation of tetrahedral intermediate mimic inhibitors of 3-deoxy-d-manno-octulosonate 8-phosphate synthase

  摘要：

  3-Deoxy-o-manno-octulosonate 8-phosphate (KDO8P) synthase catalyses the first committed step in the biosynthesis of 3-deoxy-D-manno-octulosonate (KDO), an important component of the lipopolysaccharide of Gram-negative bacteria. The pathway for KDO biosynthesis has been identified as a potential target of antibacterial drug design. The reaction catalysed by KDO8P synthase is an aldol-like condensation between phosphoenolpyruvate (PEP) and D-arabinose 5-phosphate (ASP) and proceeds through a bis-phosphorylated tetrahedral intermediate. In this study a bisphosphate analogue of the tetrahedral intermediate was synthesised and was found to inhibit the metal-dependent KDO8P synthase from Neisseria meningitidis and the metal-dependent KDO8P synthase from Acidithiobacillus ferrooxidans with inhibition constants in the low micromolar range. Additionally, monophosphorylated inhibitors were synthesised to determine the relative importance of the two phosphate groups of this bisphosphate analogue for enzyme inhibition. The removal of either of these two phosphate groups gave less potent inhibitors for both enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.025