[(2R)-2-hexadecanoyloxy-3-[hydroxy-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphoryl]oxypropyl] hexadecanoate | 28366-80-5

• 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: [(2R)-2-hexadecanoyloxy-3-[hydroxy-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphoryl]oxypropyl] hexadecanoate
• 英文别名: 1,2-dipalmitoyl-sn-glycero-3-phospho-1'-myo-inositol；dipalmitoyl L-α-phosphatidyl-D-myo-inositol；dipalmitoylphosphatidylinositol；1-O-(1',2'-Dipalmytoyl-sn-glyceryl-3'-phosphoryl)-sn-myoinositol
• CAS: 28366-80-5
• 化学式: C₄₁H₇₉O₁₃P
• 分子量: 811.044
• InChiKey: IBUKXRINTKQBRQ-KCKFLZCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  55.0
• 可旋转键数：
  36.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  209.51
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [(2R)-2-hexadecanoyloxy-3-[hydroxy-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphoryl]oxypropyl] hexadecanoate 在 甲胺 作用下， 以 甲醇 、 甲苯 、 正丁醇 为溶剂， 反应 3.0h， 生成 sn-glycero-3-phospho-(1'-myo-inositol)
  参考文献：
  名称：

  Synthesis of Inositol Phosphodiesters by Phospholipase C-Catalyzed Transesterification

  摘要：

  Transesterification of primary alcohols with inositol 1,2-cyclic phosphate (IcP) in the presence of phosphatidylinositol-specific phospholipase C (PI-PLC) resulted in the formation of O-alkyl inositol 1-phosphates. The starting IcP was obtained in a single step by PI-PLC catalyzed cleavage of phosphatidylinositol from the soybean phospholipid. The transesterification reaction was performed with a series of 20 structurally diverse hydroxyl compounds, ranging in the structural complexity from methanol to the serine-containing Ser-Tyr-Ser-Met tetrapeptide, to give the corresponding phosphodiesters with 20-80% yields, depending mainly on the solubility of alcohols in water. The rates of transesterifications, and of the competing hydrolysis of IcP to inositol 1-phosphate (IP), were relatively insensitive to the alcohol structure. With polyhydroxyl compounds such as glycerol and hexitols, the enzyme displayed complete preference toward formation of the inositol phosphate derivatives of the primary hydroxyl groups. On the other hand, PI-PLC did not discriminate between primary hydroxyl groups in different environments and showed low stereoselectivity with racemic alcohols featuring a chiral center at the beta-position, The O-alkyl inositol phosphates formed were readily separable from the hydrolytic product, IP, by the anion-exchange chromatography, and were fully characterized by means of H-1 and P-31 NMR and electrospray MS. Our results provide a new, simple, and efficient two-step synthetic route to substituted O-alkyl inositol phosphates from inexpensive starting materials. The reported reaction was successfully applied to synthesis of complex inositol phosphate derivatives, as illustrated by inositol phosphoesters of mono- and oligosaccharides, nucleosides and peptides. The synthetic usefulness of this reaction, however, is not limited to the examples shown. Because transesterification activity of phospholipase C has not been reported before, its mechanism is discussed in a broad context of mechanisms of phosphoesterases.

  DOI：

  10.1021/ja9616084
• 作为产物：
  描述：

  4-(1-甲基丙基)联苯基 生成 [(2R)-2-hexadecanoyloxy-3-[hydroxy-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphoryl]oxypropyl] hexadecanoate
  参考文献：
  名称：

  Klyashchitskii,B.A. et al., Journal of general chemistry of the USSR, 1971, vol. 41, p. 1391 - 1397

  摘要：

  DOI：

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。
• The key entity of a DCAR agonist, phosphatidylinositol mannoside Ac₁PIM₁: its synthesis and immunomodulatory function
  作者：Yohei Arai、Shota Torigoe、Takanori Matsumaru、Sho Yamasaki、Yukari Fujimoto

  DOI：10.1039/c9ob02724f

  日期：——

  Ac1PIM1 is a potential biosynthetic intermediate for phosphatidylinositol mannosides (PIMs) from Mycobacterium tuberculosis. We achieved the first synthesis of Ac1PIM1 by utilizing an allyl-type protecting group strategy and regioselective phosphorylation of inositol. A very potent agonist of an innate immune receptor DCAR, which is better than previously known agonists, is demonstrated.

  Ac1PIM1是来自结核分枝杆菌的磷脂酰肌醇甘露糖苷（PIM）的潜在生物合成中间体。我们通过利用烯丙基型保护基策略和肌醇的区域选择性磷酸化实现了Ac1PIM1的首次合成。证明了先天免疫受体DCAR的非常有效的激动剂，其比以前已知的激动剂更好。
• Improved syntheses of inositol phospholipid analogues
  作者：Martin Jones、Kishore K. Rana、John G. Ward、Rodney C. Young

  DOI：10.1016/s0040-4039(01)93785-2

  日期：1989.1
• Synthesis of Inositol Phosphodiesters by Phospholipase C-Catalyzed Transesterification
  作者：Karol S. Bruzik、Zhiwen Guan、Suzette Riddle、Ming-Daw Tsai

  DOI：10.1021/ja9616084

  日期：1996.1.1

  Transesterification of primary alcohols with inositol 1,2-cyclic phosphate (IcP) in the presence of phosphatidylinositol-specific phospholipase C (PI-PLC) resulted in the formation of O-alkyl inositol 1-phosphates. The starting IcP was obtained in a single step by PI-PLC catalyzed cleavage of phosphatidylinositol from the soybean phospholipid. The transesterification reaction was performed with a series of 20 structurally diverse hydroxyl compounds, ranging in the structural complexity from methanol to the serine-containing Ser-Tyr-Ser-Met tetrapeptide, to give the corresponding phosphodiesters with 20-80% yields, depending mainly on the solubility of alcohols in water. The rates of transesterifications, and of the competing hydrolysis of IcP to inositol 1-phosphate (IP), were relatively insensitive to the alcohol structure. With polyhydroxyl compounds such as glycerol and hexitols, the enzyme displayed complete preference toward formation of the inositol phosphate derivatives of the primary hydroxyl groups. On the other hand, PI-PLC did not discriminate between primary hydroxyl groups in different environments and showed low stereoselectivity with racemic alcohols featuring a chiral center at the beta-position, The O-alkyl inositol phosphates formed were readily separable from the hydrolytic product, IP, by the anion-exchange chromatography, and were fully characterized by means of H-1 and P-31 NMR and electrospray MS. Our results provide a new, simple, and efficient two-step synthetic route to substituted O-alkyl inositol phosphates from inexpensive starting materials. The reported reaction was successfully applied to synthesis of complex inositol phosphate derivatives, as illustrated by inositol phosphoesters of mono- and oligosaccharides, nucleosides and peptides. The synthetic usefulness of this reaction, however, is not limited to the examples shown. Because transesterification activity of phospholipase C has not been reported before, its mechanism is discussed in a broad context of mechanisms of phosphoesterases.
• Klyashchitskii,B.A. et al., Journal of general chemistry of the USSR, 1971, vol. 41, p. 1391 - 1397
  作者：Klyashchitskii,B.A. et al.

  DOI：——

  日期：——