1-棕榈酰-2-月桂酰基卵磷脂 | 82765-47-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: 1-棕榈酰-2-月桂酰基卵磷脂
• 英文名称: 1-palmitoyl-2-lauroyl-sn-glycerol-3-phosphocholine
• 英文别名: 1-Hexadecanoyl-2-dodecanoyl-sn-glycero-3-phosphocholine；[(2R)-2-dodecanoyloxy-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 82765-47-7
• 化学式: C₃₆H₇₂NO₈P
• 分子量: 677.943
• InChiKey: OVRJLLUJKRFEBG-UUWRZZSWSA-N

物化性质

• 溶解度：
  乙醇：25mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  46
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 储存条件：
  -20°C，密闭保存，干燥Conditions: -20°C, store sealed and dry.

制备方法与用途

Palmitoyl-2-lauroyl-sn-glycero-3-phosphocholine (PLPC) is a phospholipid that contains palmitoyl (16:0) acyl substituents at the sn-1 position and lauryl (12:0) acyl substituents at the sn-2 position.

反应信息

• 作为产物：
  描述：

  1-棕榈酰-2-月桂酰-锡-甘油 在 三乙胺 作用下， 以 乙腈 、 苯 为溶剂， 反应 32.0h， 生成 1-棕榈酰-2-月桂酰基卵磷脂
  参考文献：
  名称：

  A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of l-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives

  摘要：

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.

  DOI：

  10.1021/jo990414e

文献信息

• 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 and Characterization of a Major Liver Lysophosphatidylcholine Acyltransferase
  作者：Yang Zhao、Yan-Qun Chen、Tabetha M. Bonacci、David S. Bredt、Shuyu Li、William R. Bensch、David E. Moller、Mark Kowala、Robert J. Konrad、Guoqing Cao

  DOI：10.1074/jbc.m710422200

  日期：2008.3

  Phosphatidylcholine (PC) is synthesized through the Kennedy pathway, but more than 50% of PC is remodeled through the Lands cycle, i.e. the deacylation and reacylation of PC to attain the final and proper fatty acids within PC. The reacylation step is catalyzed by lysophosphatidylcholine acyltransferase (LPCAT), and we report here the identification of a novel LPCAT, which we named LPCAT3. LPCAT3 belongs to the membrane-bound O-acyltransferase (MBOAT) family and encodes a protein of 487 amino acids with a calculated molecular mass of 56 kDa. Membranes from HEK293 cells overexpressing LPCAT3 showed significantly increased LPCAT activity as assessed by thin layer chromatography analysis with substrate preference toward unsaturated fatty acids. LPCAT3 is localized within the endoplasmic reticulum and is primarily expressed in metabolic tissues including liver, adipose, and pancreas. In a human hepatoma Huh7 cells, RNA interference-mediated knockdown of LPCAT3 resulted in virtually complete loss of membrane LPCAT activity, suggesting that LPCAT3 is primarily responsible for hepatic LPCAT activity. Furthermore, peroxisome proliferator-activated receptor alpha agonists dose-dependently regulated LPCAT3 in liver in a peroxisome proliferatoractivated receptor alpha-dependent fashion, implicating a role of LPCAT3 in lipid homeostasis. Our studies identify a long-sought enzyme that plays a critical role in PC remodeling in metabolic tissues and provide an invaluable tool for future investigations on how PC remodeling may potentially impact glucose and lipid homeostasis.
• 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.
• MIXTURE OF AMPHIPATHIC MOLECULES AND METHOD FOR MODIFYING CELL MEMBRANES BY MEANS OF FUSION
  申请人：Hoffmann Bernd

  公开号：US20120100077A1

  公开（公告）日：2012-04-26

  Disclosed is a mixture of amphipathic molecules and a method for modifying cells in vivo by way of membrane fusion with these molecules.
• A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of <scp>l</scp>-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives
  作者：Farzaneh S. Roodsari、Dongpei Wu、Gregory S. Pum、Joseph Hajdu

  DOI：10.1021/jo990414e

  日期：1999.10.1

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.