Phosphoric acid hexadecyl ester (3aR,4S,4aR,7aS,8S,8aR)-8-hydroxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester phenyl ester | 161105-02-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: Phosphoric acid hexadecyl ester (3aR,4S,4aR,7aS,8S,8aR)-8-hydroxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester phenyl ester
• CAS: 161105-02-8
• 化学式: C₃₄H₅₇O₉P
• 分子量: 640.795
• InChiKey: NIICHRSUXCNPFE-LYERNRQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.47
• 重原子数：
  44.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid hexadecyl ester (3aR,4S,4aR,7aS,8S,8aR)-8-hydroxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester phenyl ester 在 platinum(IV) oxide 氢气 作用下， 反应 2.0h， 生成 1(3)-O-n-hexadecylphosphoryl-D-myo-isonitol
  参考文献：
  名称：

  Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues

  摘要：

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.

  DOI：

  10.1016/0223-5234(94)90146-5
• 作为产物：
  描述：

  (D)-1,2:4,5-di-O-isopropylidene-myo-inositol 在 吡啶 、 MSNT 、 三乙胺 作用下， 反应 2.0h， 生成 Phosphoric acid hexadecyl ester (3aR,4S,4aR,7aS,8S,8aR)-8-hydroxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl ester phenyl ester
  参考文献：
  名称：

  Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues

  摘要：

  Analogues of phosphatidylinositol (Ptdlns, 1) have been synthesized to investigate the structural requirements for inhibition of a Ptdlns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 Stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by Ptdlns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature, however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (Ptdlns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit Ptdlns 4-kinase may suggest that such species have a regulatory role in Ptdlns turnover.

  DOI：

  10.1016/0223-5234(94)90146-5