2-O-oleoyl-1-O-palmitoyl-3-O-phosphoryl-sn-glycerol | 62600-81-1

• 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: 2-O-oleoyl-1-O-palmitoyl-3-O-phosphoryl-sn-glycerol
• 英文别名: 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphate；1-palmitoyl-2-oleoyl-sn-glycero-3-phosphate；1-palmitoyl-2-oleoylphosphatidic acid；1-palmitoyl-2-oleoyl-PA；16:0 –18:1 PA；PA(16:0/18:1(n-9))；[(2R)-1-hexadecanoyloxy-3-phosphonooxypropan-2-yl] (Z)-octadec-9-enoate
• CAS: 62600-81-1
• 化学式: C₃₇H₇₁O₈P
• 分子量: 674.94
• InChiKey: OPVZUEPSMJNLOM-QEJMHMKOSA-N

物化性质

• 沸点：
  725.2±70.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿：5mg/mL
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  46
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-O-oleoyl-1-O-palmitoyl-3-O-phosphoryl-sn-glycerol 在 水 作用下， 生成 1-O-palmitoyl-2-[(9z)-octadenoyl]-glycerol
  参考文献：
  名称：

  Liposome-mediated enzymatic synthesis of phosphatidylcholine as an approach to self-replicating liposomes

  摘要：

  The four enzymes of the salvage pathway for phosphatidylcholine synthesis sn-glycerol-3-phosphate acyltransferase, 1-acyl-sn-glycerol-3-phosphate acyltransferase, phosphatidate phosphatase, and cytidinediphosphocholine phosphocholinetransferase were simulataneously bound to soybean phosphatidylcholine liposomes. Evidence is presented that the entire enzyme chain is reconstituted in the liposomes, and that synthesis is preferentially localized in the proteliposomal membrane where the enzymes are present in an active bound form. Various phosphatidylcholines, differing in the alkyl group of the fatty acid moieties, can be synthesized in this way and incorporated into the host liposomes, with a corresponding change of the equilibrium size of the liposomes. The present system can then also be seen as a self-reproducing liposome, and the implication of this for chemical autopoiesis is briefly discussed.

  DOI：

  10.1021/ja00021a043
• 作为产物：
  描述：

  3-O-di-tert-butylphosphoryl-2-O-oleoyl-1-O-palmitoyl-sn-glycerol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以100%的产率得到2-O-oleoyl-1-O-palmitoyl-3-O-phosphoryl-sn-glycerol
  参考文献：
  名称：

  Efficient Synthesis of Phospholipids from Glycidyl Phosphates

  摘要：

  New efficient routes to enantiopure phospholipids, starting from (S)-glycidol, are described. Lysophosphatidic acids and phosphatidic acids were obtained in good overall yields from (S)-glycidol, in only three and four steps, respectively. Moreover, the strategy can also be used to produce phosphatidylcholines in three steps. Using dialkylphosphoramidites, (S)-glycidol was phosphorylated to give (R)-1-O-glycidyl dialkyl phosphates. Regiospecific epoxide opening, using hexadecanol or cesium palmitate, followed by phosphate deprotection, provided lysophosphatidic acids. 2-O-Esterification prior to phosphate deprotection provided 1,2-O-diacyl and 1-O-alkyl-2-O-acyl phosphatidic acids. Phosphorylation of (S)-glycidol using phosphorus oxychloride followed by in situ treatment with choline tosylate produced (R)-glycidyl phosphocholine. Subsequent nucleophilic opening of the epoxide using cesium palmitate produced 1-O-palmitoyl-sn-glycero-3-phosphocholine, which has been used in syntheses of phosphatidylcholines.

  DOI：

  10.1021/jo010734+

文献信息

• Structural Characterization of Oxidized Glycerophosphatidylserine: Evidence of Polar Head Oxidation
  作者：Elisabete Maciel、Raquel Nunes da Silva、Cláudia Simões、Pedro Domingues、M. Rosário M. Domingues

  DOI：10.1007/s13361-011-0194-9

  日期：2011.10.1

  Non-oxidized phosphatidylserine (PS) is known to play a key role in apoptosis but there is considerable research evidence suggesting that oxidized PS also plays a role in this event, leading to the increasing interest in studying PS oxidative modifications. In this work, different PS (1-palmitoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (PLPS), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS), and 1,2-dipalmitoyl-sn-glycero-3-phospho-L-serine (DPPS) were oxidized in vitro by hydroxyl radical, generated under Fenton reaction conditions, and the reactions were monitored by ESI-MS in negative mode. Oxidation products were then fractionated by thin layer chromatography (TLC) and characterized by tandem mass spectrometry (MS/MS). This approach allowed the identification of hydroxyl, peroxy, and keto derivatives due to oxidation of unsaturated fatty acyl chains. Oxidation products due to oxidation of serine polar head were also identified. These products, with lower molecular weight than the non-modified PS, were identified as [M – 29 – H]– (terminal acetic acid), [M – 30 – H]– (terminal acetamide), [M – 13 – H]– (terminal hydroperoxyacetaldehyde), and [M – 13 – H]– (terminal hydroxyacetaldehyde plus hydroxy fatty acyl chain). Phosphatidic acid was also formed in these conditions. These findings confirm the oxidation of the serine polar head induced by the hydroxyl radical. The identification of these modifications may be a valuable tool to evaluate phosphatidylserine alteration under physiopathologic conditions and also to help understand the biological role of phosphatidylserine oxidation in the apoptotic process and other biological functions.

  未氧化的磷脂酰丝氨酸（PS）已知在细胞凋亡中发挥关键作用，但大量研究证据表明，氧化的PS在这一事件中也起着作用，因此研究PS氧化修饰的兴趣日益增加。在本研究中，不同类型的PS（1-棕榈酰基-2-亚油酰基-sn-甘油-3-磷酸-L-丝氨酸（PLPS）、1-棕榈酰基-2-油酰基-sn-甘油-3-磷酸-L-丝氨酸（POPS）和1,2-二棕榈酰基-sn-甘油-3-磷酸-L-丝氨酸（DPPS））在体外通过在芬顿反应条件下产生的羟基自由基进行氧化，并通过负模式电子喷雾质谱（ESI-MS）监测反应。氧化产物随后通过薄层色谱（TLC）分离，并通过串联质谱（MS/MS）进行表征。这种方法使得能够鉴定由于不饱和脂肪酰链氧化而产生的羟基、过氧基和酮衍生物。同时，丝氨酸极性头部氧化产生的氧化产物也得到了鉴定。这些低于未修饰PS分子量的产物被鉴定为[M – 29 – H]–（末端乙酸）、[M – 30 – H]–（末端乙酰胺）、[M – 13 – H]–（末端过氧乙醛）和[M – 13 – H]–（末端羟基乙醛加羟基脂肪酰链）。在这些条件下，磷脂酸也被形成。这些发现确认了羟基自由基诱导的丝氨酸极性头部的氧化。这些修饰的鉴定可能是评估生理病理条件下磷脂酰丝氨酸改变的有价值工具，并有助于理解磷脂酰丝氨酸氧化在凋亡过程及其他生物功能中的生物学作用。
• Compositions and methods for treating transplants
  申请人：——

  公开号：US20040213766A1

  公开（公告）日：2004-10-28

  Methods and compositions for protecting transplants from immunorejection are provided.

  本发明提供了用于保护移植物免受免疫排斥的方法和组合物。
• Polypeptides of pseudomonas aeruginosa
  申请人：ID Biomedical Corporation

  公开号：EP1790659A2

  公开（公告）日：2007-05-30

  The present invention is related to polypeptides, more particularly SPA-1, SPA-2 and SPA-3 polypeptides of Pseudomonas aeruginosa which may be used to prevent, diagnose and/or treat Pseudomonas aeruginosa infection.

  本发明涉及可用于预防、诊断和/或治疗铜绿假单胞菌感染的多肽，尤其是铜绿假单胞菌的 SPA-1、SPA-2 和 SPA-3 多肽。
• Novel neutral (bio)material
  申请人：Centre National de la Recherche Scientifique (CNRS)

  公开号：EP2444464A1

  公开（公告）日：2012-04-25

  The instant invention concerns - a method for preparing a material comprising the following steps of a) treating the support to obtain a layer having SiH function, b) grafting the SiH layer obtained in step a) with an alkene and a catalyst for covalently bonding the alkene to the coating, said alkene being non-terminal and/or having an hydrophilic part, and c) recovering a material comprising a support coated with a chain covalently grafted with Si-C bonds, - a material comprising a support, optionally comprising a polyhydrosiloxane layer, on which surface is covalently bonded a grafted chain, wherein the covalent bonding between the support and/or the polyhydrosiloxane and the chain is an Si-C bond, and the grafted chain is bonded through a non-terminal carbon, through more than one covalent bond and/or the chain is having at least one hydrophilic part, and - devices comprising such material.

  本发明涉及 - 一种制备材料的方法，包括以下步骤 a) 处理支持物以获得具有 SiH 功能的层；b) 将步骤 a) 中获得的 SiH 层与烯烃和催化剂接枝，以将烯烃共价键合到涂层上，所述烯烃为非末端烯烃和/或具有亲水部分；以及 c) 回收一种材料，该材料包括涂有共价键合的 Si-C 键接枝链的支持物、 - 一种材料，包括支撑体，可选择包括聚氢硅氧烷层，在支撑体表面共价键合了一条接枝链，其中支撑体和/或聚氢硅氧烷与链之间的共价键合是 Si-C 键，接枝链通过非末端碳键、通过一个以上的共价键和/或链具有至少一个亲水部分键合，以及 - 包括这种材料的装置。
• Compositions and methods for enhancing contrast in imaging
  申请人：Marval Biosciences, Inc.

  公开号：EP2578237A1

  公开（公告）日：2013-04-10

  Example compositions of liposomes with hydrophilic polymers on their surface, and containing relatively high concentrations of contrast- enhancing agents for computed tomography are provided. Example pharmaceutical compositions of such liposomes, when administered to a subject, provide for increased contrast of extended duration, as measured by computed tomography, in the bloodstream and other tissues of the subject. Also provided are example methods for making liposomes containing high concentrations of contrast-enhancing agents, and example methods for using the compositions.

  本发明提供了一些脂质体组合物实例，这些脂质体表面具有亲水性聚合物，并含有相对高浓度的计算机断层扫描造影剂。这种脂质体的药物组合物范例在给受试者用药时，可使受试者血液和其他组织中的对比度增加，持续时间延长，如计算机断层扫描所测。此外，还提供了制造含有高浓度造影剂的脂质体的示例方法，以及使用这些组合物的示例方法。