ethyl diisopropyl 1,4-difluoro-4-phosphonobutyrate

• 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: ethyl diisopropyl 1,4-difluoro-4-phosphonobutyrate
• 英文别名: Ethyl 4-di(propan-2-yloxy)phosphoryl-4,4-difluorobutanoate
• 化学式: C₁₂H₂₃F₂O₅P
• 分子量: 316.282
• InChiKey: OHGYMCGUGFSOBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diisopropyl difluoromethanephosphonate 、 ethyl diisopropyl 1,4-difluoro-4-phosphonobutyrate 在 lithium diisopropyl amide 作用下， 生成 tetraisopropyl 1,1,5,5-tetrafluoro-2-oxo-pentane-1,5-bisphosphonate
  参考文献：
  名称：

  Highly Potent Bisphosphonate Ligands for Phosphoglycerate Kinase

  摘要：

  We have synthesized a series of novel analogs of 1,3-bisphospho-D-glyceric -acid, 1,3-BPG,(3) and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methane-phosphonic acids replace the two phosphate monoesters of 1,3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1,3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for PKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.

  DOI：

  10.1021/jm970839y
• 作为产物：
  描述：

  diisopropyl difluoromethanephosphonate 、 丙烯酸乙酯 在 lithium diisopropyl amide 作用下， 生成 ethyl diisopropyl 1,4-difluoro-4-phosphonobutyrate
  参考文献：
  名称：

  Highly Potent Bisphosphonate Ligands for Phosphoglycerate Kinase

  摘要：

  We have synthesized a series of novel analogs of 1,3-bisphospho-D-glyceric -acid, 1,3-BPG,(3) and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methane-phosphonic acids replace the two phosphate monoesters of 1,3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1,3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for PKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.

  DOI：

  10.1021/jm970839y

文献信息

• Highly Potent Bisphosphonate Ligands for Phosphoglycerate Kinase
  作者：David L. Jakeman、Andrew J. Ivory、Michael P. Williamson、G. Michael Blackburn

  DOI：10.1021/jm970839y

  日期：1998.11.1

  We have synthesized a series of novel analogs of 1,3-bisphospho-D-glyceric -acid, 1,3-BPG,(3) and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methane-phosphonic acids replace the two phosphate monoesters of 1,3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1,3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for PKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.