1-O-hexadecanoyl-2-O-hexanoyl-sn-glycero-3-phosphocholine | 77444-40-7

• 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: 1-O-hexadecanoyl-2-O-hexanoyl-sn-glycero-3-phosphocholine
• 英文别名: Palm-C6PC；1-Hexadecanoyl-2-hexanoyl-sn-glycero-3-phosphorylcholin；1-Hexadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholine；[(2R)-3-hexadecanoyloxy-2-hexanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 77444-40-7
• 化学式: C₃₀H₆₀NO₈P
• 分子量: 593.782
• InChiKey: RBJYEKYJPBLOJX-MUUNZHRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  40
• 可旋转键数：
  30
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  甘磷酸胆碱 在 4-二甲氨基吡啶 、 二正丁基氧化锡 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 21.25h， 生成 1-O-hexadecanoyl-2-O-hexanoyl-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  混合短/长链甘油磷酸胆碱的实用选择性合成。

  摘要：

  甘油磷酰胆碱（GPC）被转化为环状亚锡衍生物，其选择性地被酰化为1-酰基-2-溶血甘油磷酸胆碱。使用2-丙醇中的C-2至C-16酰氯，该反应有效。更换溶剂后，使用酸酐的二氯甲烷溶液对溶血磷脂（lyso-PL）进行第二次酰化反应。以高收率和选择性获得了一系列的1（2）-短-2（1）-长二酰基-甘油磷酸胆碱。未检测到二酰化产物。为了检测具有酰基链的反向排列的混合链脂质，首先引入长链，然后通过NMR比较由此得到的异构体化合物。为了确定异构体化合物的位置纯度，开发了NMR方法。

  DOI：

  10.1016/j.chemphyslip.2007.03.008

文献信息

• Discrimination of Chain Positions in Mixed Short/Long-Chain Glycerophosphocholines by NMR Chemical Shift Variations
  作者：Paola D’Arrigo、Andrea Mele、Cristina Rossi、Davide Tessaro、Stefano Servi

  DOI：10.1007/s11746-008-1280-4

  日期：2008.11

  AbstractThe synthesis of a series of (1,2‐) mixed short/long‐chain glycerophosphocholines has been performed. Starting from glycerophosphorylcholine (GPC), and using regioselective acylation in the presence of dibutyltin oxide, a set of high‐purity isomeric mixed‐chain phospholipids was obtained. This has allowed the development of a simple NMR method for the structural determination of the isomeric 1(2)‐short‐2(1)‐long‐diacylglycerophosphocholines. The method is based on the observation that selected protons in the two series of isomeric phospholipids undergo systematic chemical shift variations Δδ that can be ascribed to the acyl substituents on the glycerol backbone. The observed patterns can be exploited as a simple method for the discrimination of regioisomeric unsymmetrical 1,2‐diacylglycerophosphocholines.
• Cloning and Characterization of Mouse Lung-type Acyl-CoA:Lysophosphatidylcholine Acyltransferase 1 (LPCAT1)
  作者：Hiroki Nakanishi、Hideo Shindou、Daisuke Hishikawa、Takeshi Harayama、Rie Ogasawara、Akira Suwabe、Ryo Taguchi、Takao Shimizu

  DOI：10.1074/jbc.m600225200

  日期：2006.7

  Phosphatidylcholine (1,2-diacyl-sn-glycero-3-phosphocholine, PC), is an important constituent of biological membranes. It is also the major component of serum lipoproteins and pulmonary surfactant. In the remodeling pathway of PC biosynthesis, 1-acyl-sn-glycero-3- phosphocholine (LPC) is converted to PC by acyl-CoA:lyso-phosphatidylcholine acyltransferase (LPCAT, EC 2.3.1.23). Whereas LPCAT activity has been detected in several tissues, the structure and detailed biochemical information on the enzyme have not yet been reported. Here, we present the cloning and characterization of a cDNA for mouse lung-type LPCAT (LPCAT1). The cDNA encodes an enzyme of 60kDa, with three putative transmembrane domains. When expressed in Chinese hamster ovary cells, mouse LPCAT1 exhibited Ca2(+)-independent activity with a pH optimum between 7.4 and 10. LPCAT1 demonstrated a clear preference for saturated fatty acyl-CoAs, and 1-myristoyl- or 1-palmitoyl-LPC as acyl donors and acceptors, respectively. Furthermore, the enzyme was predominantly expressed in the lung, in particular in alveolar type II cells. Thus, the enzyme might synthesize phosphatidylcholine in pulmonary surfactant and play a pivotal role in respiratory physiology.
• Identification of a Novel Noninflammatory Biosynthetic Pathway of Platelet-activating Factor*
  作者：Takeshi Harayama、Hideo Shindou、Rie Ogasawara、Akira Suwabe、Takao Shimizu

  DOI：10.1074/jbc.m708909200

  日期：2008.4

  Platelet-activating factor (PAF) is a potent lipid mediator playing various inflammatory and physiological roles. PAF is biosynthesized through two independent pathways called the de novo and remodeling pathways. Lyso-PAF acetyltransferase (lyso-PAF AT) was believed to biosynthesize PAF under inflammatory conditions, through the remodeling pathway. The first isolated lyso-PAF AT (LysoPAFAT/LPCAT2) had consistent properties. However, we show in this study the finding of a second lyso-PAF AT working under noninflammatory conditions. We partially purified a Ca2+-independent lyso-PAF AT from mouse lung. Immunoreactivity for lysophosphatidylcholine acyltransferase 1 (LPCAT1) was detected in the active fraction. Lpcat1-transfected Chinese hamster ovary cells exhibited both LPCAT and lyso-PAF AT activities. We confirmed that LPCAT1 transfers acetate from acetyl-CoA to lyso-PAF by the identification of an acetyl-CoA (and other acyl-CoAs) interacting site in LPCAT1. We further showed that LPCAT1 activity and expression are independent of inflammatory signals. Therefore, these results suggest the molecular diversity of lyso-PAF ATs is as follows: one (LysoPAFAT/LPCAT2) is inducible and activated by inflammatory stimulation, and the other (LPCAT1) is constitutively expressed. Each lyso-PAF AT biosynthesizes inflammatory and physiological amounts of PAF, depending on the cell type. These findings provide important knowledge for the understanding of the diverse pathological and physiological roles of PAF.
• A practical selective synthesis of mixed short/long chains glycerophosphocholines
  作者：Paola D’Arrigo、Ezio Fasoli、Giuseppe Pedrocchi-Fantoni、Cristina Rossi、Caterina Saraceno、Davide Tessaro、Stefano Servi

  DOI：10.1016/j.chemphyslip.2007.03.008

  日期：2007.6

  1-acyl-2-lyso-glycerophosphocholines. The reaction is effective using C-2 to C-16 acid chlorides in 2-propanol. After solvent replacement the lyso-phospholipid (lyso-PL) is subjected to a second acylation using acid anhydrides in methylene chloride. A series of 1(2)-short-2(1)-long-diacyl-glycerophosphocholines are obtained in high yields and selectivity. No diacylation product was detected. In order to detect

  甘油磷酰胆碱（GPC）被转化为环状亚锡衍生物，其选择性地被酰化为1-酰基-2-溶血甘油磷酸胆碱。使用2-丙醇中的C-2至C-16酰氯，该反应有效。更换溶剂后，使用酸酐的二氯甲烷溶液对溶血磷脂（lyso-PL）进行第二次酰化反应。以高收率和选择性获得了一系列的1（2）-短-2（1）-长二酰基-甘油磷酸胆碱。未检测到二酰化产物。为了检测具有酰基链的反向排列的混合链脂质，首先引入长链，然后通过NMR比较由此得到的异构体化合物。为了确定异构体化合物的位置纯度，开发了NMR方法。