1D-1-(1',2'-di-O-hexadecanoyl-sn-glycero(3')phsopho)-myo-inositol 3,5-bis(phosphate)

• 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-(1',2'-di-O-hexadecanoyl-sn-glycero(3')phsopho)-myo-inositol 3,5-bis(phosphate)
• 英文别名: dipalmitoyl-L-α-phosphatidyl-D-myo-inositol 3,5-bisphosphate；phosphatidylinositol 3,5-bisphosphate
• 化学式: C₄₁H₈₁O₁₉P₃
• 分子量: 971.004
• InChiKey: UZMPYXSDDZXMAI-LNNNXZRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.96
• 重原子数：
  63.0
• 可旋转键数：
  40.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  302.57
• 氢给体数：
  8.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  (+)-benzyloxy(N,N-diisopropylamino)(1,2-di-O-hexadecanoyl-sn-glycer-3-yl)phosphine 在 palladium hydroxide - carbon 氢气 作用下， 以 叔丁醇 为溶剂， 以85%的产率得到1D-1-(1',2'-di-O-hexadecanoyl-sn-glycero(3')phsopho)-myo-inositol 3,5-bis(phosphate)
  参考文献：
  名称：

  l-α-Phosphatidyl-d-myo-inositol 3,5-bisphosphate: total synthesis of a new inositol phospholipid via myo-inositol orthoacetate

  摘要：

  The synthesis from myo-inositol of a newly-discovered inositol phospholipid, phosphatidylinositol 3,5-bisphosphate [PtdIns(3,5)P-2], is described. The synthetic strategy, employing inter alia, a trimethylaluminium-mediated regioselective cleavage of a protected inyo-inositol orthoacetate followed by an optical resolution using (R)-(-)-5-oxo-2-tetrahydrofurancarboxylate esters, allows rapid access to dipalmitoyl PtdIns(3,5)P-2. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01422-1

文献信息

• Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes
  作者：Stuart J. Conway、James Gardiner、Simon J. A. Grove、Melloney K. Johns、Ze-Yi Lim、Gavin F. Painter、Diane E. J. E. Robinson、Christine Schieber、Jan W. Thuring、Leon S.-M. Wong、Meng-Xin Yin、Antony W. Burgess、Bruno Catimel、Phillip T. Hawkins、Nicholas T. Ktistakis、Leonard R. Stephens、Andrew B. Holmes

  DOI：10.1039/b913399b

  日期：——

  The synthesis of the complete family of phosphatidylinositol phosphate analogues (PIPs) from five key core intermediates A–E is described. These core compounds were obtained from myo-inositol orthoformate 1via regioselective DIBAL-H and trimethylaluminium-mediated cleavages and a resolution–protection process using camphor acetals 10. Coupling of cores A–E with phosphoramidites 34 and 38, derived from the requisite protected lipid side chains, afforded the fully-protected PIPs. Removal of the remaining protecting groups was achieved via hydrogenolysis using palladium black or palladium hydroxide on carbon in the presence of sodium bicarbonate to afford the complete family of dipalmitoyl- and amino-PIP analogues 42, 45, 50, 51, 58, 59, 67, 68, 76, 77, 82, 83, 92, 93, 99 and 100. Investigations using affinity probes incorporating these compounds have identified novel proteins involved in the PI3K intracellular signalling network and have allowed a comprehensive proteomic analysis of phosphoinositide interacting proteins.

  报道了从五个关键的核心中间体A-E合成完整的磷脂酰肌醇磷酸类似物（PIPs）家族的方法。这些核心化合物通过选择性DIBAL-H和三甲基铝介导的裂解以及使用樟脑乙缩醛的解析保护过程，从肌醇原甲酸1中获得。将核心A-E与从所需保护的脂质侧链衍生的磷酰胺34和38偶联，得到了完全保护的PIPs。通过使用钯黑或碳上的钯氢氧化物在碳酸氢钠存在下的氢解，去除了剩余的保护基团，得到了完整的二棕榈酰和氨基PIP类似物42、45、50、51、58、59、67、68、76、77、82、83、92、93、99和100。利用包含这些化合物的亲和探针进行的研究，鉴定了参与PI3K细胞内信号网络的新蛋白，并允许对磷脂酰肌醇相互作用蛋白进行全面的蛋白质组学分析。
• 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。
• Chemical Resolution of 1,2-O-Cyclohexylidene-3,4-O-(tetraisopropyldisiloxane-1,3-diyl)-myo-inositol and Synthesis of Phosphatidyl-D-myo-inositol 3,5-Bisphosphate from BothL- andD-Enantiomers
  作者：Fushe Han、Minoru Hayashi、Yutaka Watanabe

  DOI：10.1002/ejoc.200300517

  日期：2004.2

  Chemical resolution of a versatile starting material, 1,2-Ocyclohexylidene-3,4-O-(tetraisopropyldisiloxane-1,3-diyl)myo-inositol, which is used to access naturally occurring inositol phosphates and phosphatidylinositol phosphates, is described. Starting from both D- and L-enantiomers of the material, the synthesis of phosphatidyl-D-myo-inositol 3,5-bisphosphate [PtdIns(3,5)P2] has been conveniently

  描述了通用起始材料 1,2-Ocyclohexylidene-3,4-O-(tetraisopropyldisteroid-1,3-diyl) myo-inositol 的化学拆分，该材料用于获取天然存在的肌醇磷酸盐和磷脂酰肌醇磷酸盐。从材料的 D-和 L-对映异构体开始，磷脂酰-D-肌醇 3,5-二磷酸 [PtdIns(3,5)P2] 的合成已通过收敛途径方便地完成。合成过程中的关键反应之一是适当保护的肌醇 1,2,4-三醇衍生物的区域选择性磷酸化。在 1:12 (v/v) 吡啶/CH2Cl2 混合物中尝试磷酸化三醇根本没有进行，而在优化的溶剂系统中，吡啶/CH2Cl2 (1.1:1, v/v)，反应提供了 68%所需的 1-O-磷酸盐作为单一产品。1H NMR 光谱的进一步研究表明，三个 OH 对 1,2,4-三醇衍生物的反应性受分子间氢键的控制，这可能会被反应溶剂中吡啶比例的增加所破坏。(©
• Painter, Gavin F.; Grove, Simon J. A.; Gilbert, Lan H., Journal of the Chemical Society. Perkin transactions I, 1999, # 8, p. 923 - 935
  作者：Painter, Gavin F.、Grove, Simon J. A.、Gilbert, Lan H.、Holmes, Andrew B.、Raithby, Paul R.、Hill, Malcolm L.、Hawking, Phillip T.、Stephens, Leonard R.

  DOI：——

  日期：——
• l-α-Phosphatidyl-d-myo-inositol 3,5-bisphosphate: total synthesis of a new inositol phospholipid via myo-inositol orthoacetate
  作者：Andrew M. Riley、Barry V.L. Potter

  DOI：10.1016/s0040-4039(98)01422-1

  日期：1998.9

  The synthesis from myo-inositol of a newly-discovered inositol phospholipid, phosphatidylinositol 3,5-bisphosphate [PtdIns(3,5)P-2], is described. The synthetic strategy, employing inter alia, a trimethylaluminium-mediated regioselective cleavage of a protected inyo-inositol orthoacetate followed by an optical resolution using (R)-(-)-5-oxo-2-tetrahydrofurancarboxylate esters, allows rapid access to dipalmitoyl PtdIns(3,5)P-2. (C) 1998 Elsevier Science Ltd. All rights reserved.