Presqualene alcohol | 117182-28-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Presqualene alcohol
• 英文别名: [(1S,2S,3S)-2-[(3E)-4,8-dimethylnona-3,7-dienyl]-2-methyl-3-[(1E,5E)-2,6,10-trimethylundeca-1,5,9-trienyl]cyclopropyl]methanol
• CAS: 117182-28-2
• 化学式: C₃₀H₅₀O
• 分子量: 426.726
• InChiKey: XLTBFLSFXLLDAZ-VYCBRMPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.12
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Presqualene alcohol 在 草酰氯 、 四丁基高锰酸胺盐 、 水 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.42h， 生成 trans-2-<(3E)-4,8-dimethyl-3,7-nonadienyl>-2-methyl-trans-3-<(1E,5E)-2,6,10-trimethyl-1,5,9-undecatrienyl>cyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis of ammonium analogs of carbocationic intermediates in the conversion of presqualene diphosphate to squalene

  摘要：

  DOI：

  10.1021/jo00260a019
• 作为产物：
  描述：

  金合欢醇 在 吡啶 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 三溴化磷 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 Presqualene alcohol
  参考文献：
  名称：

  （±）-角鲨烯醇，（±）-戊烯醇和结构上相关的化合物的合成

  摘要：

  对于环丙烷环合成的碱催化加成-消除方法的立体化学，采用β γ不饱和苯基砜和αβ不饱和酯，已审查。的烯烃几何β γ不饱和砜被保留在产品中，和不饱和侧链和酯官能团出现反式围绕该环，具有相当大的立体选择性。另一方面，αβ-不饱和酯的双键的几何形状在阴离子加成产物中达到平衡。因此，基于原始αβ-不饱和酯的几何形状，在没有立体选择偏好的情况下产生了所得的环丙烷。这项工作已导致合成乙基2,2-二甲基-反式-3-[（1E，5 E）-2,6,10-三甲基十一碳烯-1,5,9-三烯基]环丙烷羧酸盐（40）和相应的环丙基甲醇（42），代表角鲨烯分子的一侧，和对C-2差向异构二萜类化合物2-[（（E））-4,8-​​二甲基壬基-3,7-二烯基] -2-甲基-反式-3-（2-甲基丙-1-烯基）环丙烷羧酸酯（44）和（45）以及相应的醇（47）和（48），代表角鲨烯分子的另一侧。还研究了较低的异戊二烯。

  DOI：

  10.1039/p19750000897

文献信息

• Enantioselective Synthesis of (+)-Presqualene Diphosphate
  作者：Daniel H. Rogers、Eugene C. Yi、C. Dale Poulter

  DOI：10.1021/jo00109a026

  日期：1995.2

  (+)-(1R,2R,3R)-Presqualene diphosphate (PSPP) is an intermediate in the biosynthesis of squalene from farnesyl diphosphate (FPP). The natural 1R,2R,3R enantiomer was synthesized from farnesol in nine steps with greater than or equal to 98% ee. The key step in the synthesis was the stereoselective intramolecular cyclopropanation of farnesyl diazoacetate (5) upon treatment with a chiral rhodium catalyst to give (-)-lactone 6.

  (+)-(1R,2R,3R)-Legalene 二磷酸（PSPP）是法呢烯二磷酸（FPP）生物合成鲨烯过程中的一个中间体。天然的1R,2R,3R 对映异构体通过从法呢醇出发的九步合成路线制得，纯度超过或等于98% ee。合成的关键步骤是法呢基叠氮醋酸酯（5）在手性铑催化剂作用下选择性的分子内环丙烷化，生成(-)-环酯6。
• Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds
  作者：E.J. Corey、J.William Suggs

  DOI：10.1016/s0040-4039(00)75204-x

  日期：1975.1
• Studies in terpene biosynthesis. Synthesis and resolution of presqualene and prephytoene alcohols
  作者：Lawrence J. Altman、Robert C. Kowerski、Dilip R. Laungani

  DOI：10.1021/ja00487a037

  日期：1978.9
• Squalene synthetase, inhibition by ammonium analogs of carbocationic intermediates in the conversion of presqualene diphosphate to squalene
  作者：C. Dale Poulter、Todd L. Capson、Michael D. Thompson、Ronda S. Bard

  DOI：10.1021/ja00192a036

  日期：1989.5
• Functional Characterization of the Atypical Integral Membrane Lipid Phosphatase PDP1/PPAPDC2 Identifies a Pathway for Interconversion of Isoprenols and Isoprenoid Phosphates in Mammalian Cells
  作者：Sumitra Miriyala、Thangaiah Subramanian、Manikandan Panchatcharam、Hongmei Ren、Mark I. McDermott、Manjula Sunkara、Tracy Drennan、Susan S. Smyth、H. Peter Spielmann、Andrew J. Morris

  DOI：10.1074/jbc.m109.083931

  日期：2010.4

  The polyisoprenoid diphosphates farnesyl diphosphate (FPP) and geranylgeranyl diphosphate (GGPP) are intermediates in the synthesis of cholesterol and related sterols by the mevalonate pathway and precursors for the addition of isoprenyl anchors to many membrane proteins. We developed tandem mass spectrometry assays to evaluate polyisoprenoid diphosphate phosphatase activity of an unusual integral membrane lipid enzyme: type 1 polyisoprenoid diphosphate phosphatase encoded by the PPAPDC2 gene (PDP1/PPAPDC2). In vitro, recombinant PDP1/PPAPDC2 preferentially hydrolyzed polyisoprenoid diphosphates, including FPP and GGPP over a variety of glycerol-and sphingo-phospholipid substrates. Overexpression of mammalian PDP1/PPAPDC2 in budding yeast depletes cellular pools of FPP leading to growth defects and sterol auxotrophy. In mammalian cells, PDP1/PPAPDC2 localizes to the endoplasmic reticulum and nuclear envelope and, unlike the structurally related lipid phosphate phosphatases, is predicted to be oriented with key residues of its catalytic domain facing the cytoplasmic face of the membrane. Studies using synthetic isoprenols with chemical properties that facilitate detection by mass spectrometry identify a pathway for interconversion of isoprenols and isoprenoid diphosphates in intact mammalian cells and demonstrate a role for PDP1/PPAPDC2 in this process. Overexpression of PDP1/PPAPDC2 in mammalian cells substantially decreases protein isoprenylation and results in defects in cell growth and cytoskeletal organization that are associated with dysregulation of Rho family GTPases. Taken together, these results focus attention on integral membrane lipid phosphatases as regulators of isoprenoid phosphate metabolism and suggest that PDP1/PPAPDC2 is a functional isoprenoid diphosphate phosphatase.