1-O-benzyl-2,3-di-O-n-dodecanoyl-sn-glycerol | 161003-45-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-O-benzyl-2,3-di-O-n-dodecanoyl-sn-glycerol
• 英文别名: [(2R)-2-dodecanoyloxy-3-phenylmethoxypropyl] dodecanoate
• CAS: 161003-45-8
• 化学式: C₃₄H₅₈O₅
• 分子量: 546.832
• InChiKey: HHUYYRVQLQCPRM-JGCGQSQUSA-N

物化性质

• 沸点：
  609.454±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.968±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  39
• 可旋转键数：
  29
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-benzyl-2,3-di-O-n-dodecanoyl-sn-glycerol 在 platinum(IV) oxide 、 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、303.98 kPa 条件下， 反应 29.0h， 生成 2,3-di-O-n-dodecanoyl-sn-glycer-1-yl phosphate
  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：

  月桂酰氯 、 (S)-(-)-3-苄氧基-1,2-丙二醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以100%的产率得到1-O-benzyl-2,3-di-O-n-dodecanoyl-sn-glycerol
  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

文献信息

• Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues
  作者：RC Young、CP Downes、M Jones、KJ Milliner、KK Rana、JG Ward

  DOI：10.1016/0223-5234(94)90146-5

  日期：1994.1

  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.