1D-1-O-(2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-O-phospho)-myo-inositol 3,4,5-trisphosphate

• 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: 1D-1-O-(2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-O-phospho)-myo-inositol 3,4,5-trisphosphate
• 英文别名: 1-O-(2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phospho)-D-myo-inositol 3,4,5-trisphosphate；sn-1-O-stearoyl-2-O-arachidonyl-D-phosphatidylinositol 3,4,5-tris(dihydrogen phosphate)；sn-2-arachidonoyl-sn-1-stearoyl-PI(3,4,5)P3
• 化学式: C₄₇H₈₆O₂₂P₄
• 分子量: 1127.08
• InChiKey: BRGYSCORDHSZEK-WWZVCVIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.52
• 重原子数：
  73.0
• 可旋转键数：
  44.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  349.1
• 氢给体数：
  9.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (R)-2-{[(1S,2S,3S,4S,5R,6S)-2-(2-chloro-acetoxy)-6-(4-oxo-pentanoyloxy)-3,4,5-tris-phosphonooxy-cyclohexyloxy]-hydroxy-phosphoryloxy}-1-octadecanoyloxymethyl-ethyl ester 在 ethyldiisopropylammonium hydrazinedithiocarbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 以73%的产率得到1D-1-O-(2-O-arachidonoyl-1-O-stearoyl-sn-glycero-3-O-phospho)-myo-inositol 3,4,5-trisphosphate
  参考文献：
  名称：

  Synthesis of PI(3,4,5)P3 with unsaturated and saturated fatty acid chains

  摘要：

  Synthesis of three PI(3,4,5)P(3)s, sn-1-O-stearoyl-sn-2-O-arachidonoyl, stearoyl-linolenoyl, and distearoyl phosphatidyl-myo-inositol 3,4,5-trisphosphate with the natural configuration for the arachidonoyl version was established by employing 9-fluorenylmethyl-protected phosphate derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00551-7

文献信息

• Comprehensive and Uniform Synthesis of All Naturally Occurring Phosphorylated Phosphatidylinositols
  作者：Robert J. Kubiak、Karol S. Bruzik

  DOI：10.1021/jo0206418

  日期：2003.2.1

  Studies of cellular signal transduction mechanisms involving receptor-mediated generation of inositol phosphates and phosphorylated phosphatidylinositols require easy access to these naturally occurring products. Although numerous synthetic methods have been developed during the past decade, most of these methods suffer from excessive length and lack of generality. In this work we describe the comprehensive

  对涉及受体介导的肌醇磷酸酯和磷酸化磷脂酰肌醇的生成的细胞信号转导机制的研究要求容易获得这些天然产物。尽管在过去的十年中已经开发了许多合成方法，但是这些方法中的大多数都存在长度过长和缺乏通用性的问题。在这项工作中，我们描述了所有天然存在的磷脂酰肌醇（例如磷脂酰肌醇，3-磷酸磷脂酰肌醇，4-磷酸酯，5-磷酸酯，3,4-双磷酸酯，3,5-双磷酸酯，4,5-双磷酸酯，和3,4,5-三磷酸酯，具有饱和和不饱和脂肪酸链。
• Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] and its diastereoisomers
  作者：Piers R. J. Gaffney、Colin B. Reese

  DOI：10.1039/b007267m

  日期：——

  The chemical synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] 2, in which the 1- and 2-hydroxy functions of the glycerol moiety are esterified with stearic and arachidonic acid, respectively, is described. The synthesis of three diastereoisomers 41, 42 and 43 of PtdIns(3,4,5)P3 is also reported.

  天然存在的磷脂酰肌醇3,4,5-三磷酸[PtdIns（3,4,5）P 3 ] 2的化学合成，其中甘油部分的1-和2-羟基官能团被硬脂酸酯和花生四烯酸分别描述。三种非对映体的合成41，42和43磷脂酰肌醇（3,4,5）的P 3也有报道。
• Synthesis of 3,4,5-trisphosphate and its stereoisomers
  作者：Piers R.J. Gaffney、Colin B. Reese

  DOI：10.1016/s0960-894x(97)10166-4

  日期：1997.12

  The chemical synthesis of PtdIns(3,4,5)P-3 2 and three of its stereoisomers is described. (C) 1997 Elsevier Science Ltd.
• Synthesis of PI(3,4,5)P3 with unsaturated and saturated fatty acid chains
  作者：Yutaka Watanabe、Mitsunobu Nakatomi

  DOI：10.1016/s0040-4020(99)00551-7

  日期：1999.8

  Synthesis of three PI(3,4,5)P(3)s, sn-1-O-stearoyl-sn-2-O-arachidonoyl, stearoyl-linolenoyl, and distearoyl phosphatidyl-myo-inositol 3,4,5-trisphosphate with the natural configuration for the arachidonoyl version was established by employing 9-fluorenylmethyl-protected phosphate derivatives. (C) 1999 Elsevier Science Ltd. All rights reserved.