Octadecanoic acid (R)-2-[benzyloxy-((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester | 195970-38-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: Octadecanoic acid (R)-2-[benzyloxy-((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester
• CAS: 195970-38-8
• 化学式: C₆₈H₁₀₉O₁₅P
• 分子量: 1197.58
• InChiKey: PJGDXFCNWIJOOB-AOPAWIEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.91
• 重原子数：
  84.0
• 可旋转键数：
  53.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  194.97
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  Octadecanoic acid (R)-2-[benzyloxy-((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester 在 四甲基乙二胺 、 1,1,2,2-四氟-1,2-二溴乙烷 、 仲丁基锂 作用下， 生成 L-α-phosphatidylinositol sodium salt
  参考文献：
  名称：

  The structural requirement of phosphatidylinositols as substrate of phosphatidylinositol 3-kinase

  摘要：

  Synthetic distearate phosphatidylinositol (PI) was not phosphorylated by PI 3-kinase. The fatty acids at glycerol sn-2 must be as short as octanoic acid or less to act as a substrate of PI 3-kinase. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00004-0
• 作为产物：
  描述：

  Octadecanoic acid (R)-2-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-tris-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryloxy}-1-octadecanoyloxymethyl-ethyl ester 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Octadecanoic acid (R)-2-[benzyloxy-((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Phosphatidyl-D-myo-inositol 3,4,5-trisphosphate.

  摘要：

  细胞信号转导中的第二信使候选物质磷脂酰-D-肌醇-3,4,5-三磷酸以同手性形式被高效合成。

  DOI：

  10.1248/cpb.45.1521

文献信息

• Phosphorylation of Unnatural Phosphatidylinositols with Phosphatidylinositol 3-Kinase
  作者：Naoko Morisaki、Koji Morita、Asuka Nishikawa、Noriyuki Nakatsu、Yasuhisa Fukui、Yuichi Hashimoto、Ryuichi Shirai

  DOI：10.1016/s0040-4020(00)00161-7

  日期：2000.4

  Phosphatidylinositol analogs (PIC2PIC18) having a series of saturated fatty acid (C2-C18) at sn-2 position were synthesized and subjected to the phosphorylation reaction with phosphatidylinositol 3-kinase (PI 3-kinase). The reactivity of PIC8 with PI 3-kinase turned out to be comparable to that of natural PI, although PIC18 was not phosphorylated under the same condition. The chirality of sn-2 center was not responsible for the phosphorylation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.