2-硬脂酰基-sn-甘油-3-磷酸胆碱 | 4421-58-3

• 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: 2-硬脂酰基-sn-甘油-3-磷酸胆碱
• 英文名称: 2-Stearoyl-sn-glycero-3-phosphocholine
• 英文别名: [(2R)-3-hydroxy-2-octadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 4421-58-3
• 化学式: C₂₆H₅₄NO₇P
• 分子量: 523.691
• InChiKey: IQGPMZRCLCCXAG-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  35
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-oleoyl-2-stearoyl-sn-glycero-3-phosphocholine 、 N-乙酰基神经鞘氨醇 生成 1-O-Oleoyl-N-acetylsphingosine 、 2-硬脂酰基-sn-甘油-3-磷酸胆碱
  参考文献：
  名称：

  溶酶体磷脂酶A2的位置特异性。

  摘要：

  溶酶体磷脂酶A（2）（Lpla2）在肺泡巨噬细胞中高度表达，并可能介导表面活性剂的磷脂代谢。对这种磷脂酶特性的研究与磷脂酶A（1）和磷脂酶A（2）活性的存在是一致的。通过生产由Lpla2的转酰酶活性产生的O-酰基化合物来研究这些活性。将含有POPC和N-乙酰基鞘氨醇（NAS）的脂质体与从稳定转染了小鼠Lpla2基因的MDCK细胞获得的可溶性级分一起孵育。Lpla2生产了两个1-O-酰基-NAS，1-O-棕榈酰基-NAS和1-O-油酰基-NAS。1-O-油酰基-NAS的形成速率是1-O-棕榈酰基-NAS的2.5倍。当使用1-油酰基-2-棕榈酰基-sn-甘油-3-磷酸胆碱（OPPC）时，1-O-油酰基-NAS的形成速率是1-O-棕榈酰基-NAS的5倍。因此，Lpla2可以在POPC和OPPC的sn-1和sn-2位置同时作用于酰基。当使用1-棕榈酰基-2-不饱和酰基-sn-甘油-3-磷酸胆碱作为

  DOI：

  10.1194/jlr.m600183-jlr200

文献信息

• Process for preparing lysophoshatidylcholine
  申请人：CHEMI S.p.A.

  公开号：EP1650215A1

  公开（公告）日：2006-04-26

  What is described is a process for preparing lysophosphatidylcholine by selective monoacylation of glycerophosphorylcholine (I), in the presence of an acylating agent and of dialkyltin derivatives, according to the following diagram: the process being particularly simple and having high overall yields.

  所描述的是通过在酰化剂和二烷基锡衍生物的存在下，通过选择性单酰化甘油磷酸胆碱（I）来制备溶血磷脂酰胆碱的过程，如下图所示： 该过程特别简单且总产率高。
• Positional specificity of lysosomal phospholipase A2
  作者：Akira Abe、Miki Hiraoka、James A. Shayman

  DOI：10.1194/jlr.m600183-jlr200

  日期：2006.10

  5-fold higher than that of 1-O-palmitoyl-NAS. Thus, Lpla2 can act on acyl groups at both sn-1 and sn-2 positions of POPC and OPPC. When 1-palmitoyl-2-unsaturated acyl-sn-glycero-3-phosphocholines were used as acyl donors, the transacylation of the acyl group from the sn-2 position to NAS was preferred to that of the palmitoyl group from the sn-1 position. An exception was observed for 1-palmitoyl-2-ar

  溶酶体磷脂酶A（2）（Lpla2）在肺泡巨噬细胞中高度表达，并可能介导表面活性剂的磷脂代谢。对这种磷脂酶特性的研究与磷脂酶A（1）和磷脂酶A（2）活性的存在是一致的。通过生产由Lpla2的转酰酶活性产生的O-酰基化合物来研究这些活性。将含有POPC和N-乙酰基鞘氨醇（NAS）的脂质体与从稳定转染了小鼠Lpla2基因的MDCK细胞获得的可溶性级分一起孵育。Lpla2生产了两个1-O-酰基-NAS，1-O-棕榈酰基-NAS和1-O-油酰基-NAS。1-O-油酰基-NAS的形成速率是1-O-棕榈酰基-NAS的2.5倍。当使用1-油酰基-2-棕榈酰基-sn-甘油-3-磷酸胆碱（OPPC）时，1-O-油酰基-NAS的形成速率是1-O-棕榈酰基-NAS的5倍。因此，Lpla2可以在POPC和OPPC的sn-1和sn-2位置同时作用于酰基。当使用1-棕榈酰基-2-不饱和酰基-sn-甘油-3-磷酸胆碱作为
• A calcium-dependent acyltransferase that produces N-acyl phosphatidylethanolamines
  作者：Yuji Ogura、William H Parsons、Siddhesh S Kamat、Benjamin F Cravatt

  DOI：10.1038/nchembio.2127

  日期：2016.9

  More than 30 years ago, a calcium-dependent enzyme activity was described that generates N-acyl phosphatidylethanolamines (NAPEs), which are precursors for N-acyl ethanolamine (NAE) lipid transmitters, including the endocannabinoid anandamide. The identity of this calcium-dependent N-acyltransferase (Ca-NAT) has remained mysterious. Here, we use activity-based protein profiling to identify the poorly

  30年前，人们描述了一种钙依赖性酶活性，可产生N-酰基磷脂酰乙醇胺（NAPE），N-酰基磷脂酰乙醇胺是N-酰基乙醇胺（NAE）脂质递质的前体，包括内源性大麻素anandamide。这种依赖钙的N-酰基转移酶（Ca-NAT）的身份一直很神秘。在这里，我们使用基于活动的蛋白质谱分析来鉴定特征不清的丝氨酸水解酶PLA2G4E作为小鼠脑Ca-NAT，并显示该酶在哺乳动物细胞中产生NAPE和NAE。
• The physical state of lipid substrates provides transacylation specificity for tafazzin
  作者：Michael Schlame、Devrim Acehan、Bob Berno、Yang Xu、Salvatore Valvo、Mindong Ren、David L Stokes、Richard M Epand

  DOI：10.1038/nchembio.1064

  日期：2012.10

  Tafazzin, the mitochondrial transacylase that is deficient in Barth syndrome, selects lipid substrates in the inverted hexagonal phase but does not react with bilayer lipids. Cardiolipin is a mitochondrial phospholipid with a characteristic acyl chain composition that depends on the function of tafazzin, a phospholipid-lysophospholipid transacylase, although the enzyme itself lacks acyl specificity. We incubated isolated tafazzin with various mixtures of phospholipids and lysophospholipids, characterized the lipid phase by 31P-NMR and measured newly formed molecular species by MS. Substantial transacylation was observed only in nonbilayer lipid aggregates, and the substrate specificity was highly sensitive to the lipid phase. In particular, tetralinoleoyl-cardiolipin, a prototype molecular species, formed only under conditions that favor the inverted hexagonal phase. In isolated mitochondria, <1% of lipids participated in transacylations, suggesting that the action of tafazzin was limited to privileged lipid domains. We propose that tafazzin reacts with non–bilayer-type lipid domains that occur in curved or hemifused membrane zones and that acyl specificity is driven by the packing properties of these domains.

  Tafazzin是线粒体转酰基酶，在巴特综合征中缺乏，它在倒六边形相中选择脂质底物，但不会与双层脂质发生反应。 心磷脂是一种线粒体磷脂，具有独特的酰基链组成，这种组成取决于tafazzin的功能，而tafazzin是一种磷脂-溶血磷脂转酰基酶，尽管酶本身缺乏酰基特异性。我们将分离的tafazzin与各种磷脂和溶血磷脂混合物一起培养，通过31P-NMR表征脂质相，并通过MS测量新形成的分子种类。仅在非双层脂质聚集物中观察到大量的转酰基化，底物特异性对脂质相高度敏感。特别是，四亚油酰基-心磷脂是一种原型分子种类，仅在有利于倒六边形相的条件下形成。在分离的线粒体中，只有不到1%的脂质参与转酰基化，这表明tafazzin的作用仅限于特权脂质域。我们提出，tafazzin与弯曲或半融合膜区域中的非双层型脂质域发生反应，而酰基特异性是由这些域的堆积特性驱动的。
• Dual-purpose PAT/ultrasound contrast agent bound with nanoparticles containing drug and method for preparing same
  申请人：IMGT CO, LTD.

  公开号：US10912848B2

  公开（公告）日：2021-02-09

  The present invention provides a dual-purpose photoacoustic tomography (PAT)/ultrasound contrast agent comprising: (a) a micro-bubble containing gas and porphyrin therein; and (b) nanoparticles bound on a surface of the micro-bubble and containing a drug. The contrast agent of the present invention can be used in both the ultrasound diagnosis and the photoacoustic image diagnosis, and can significantly increase the accuracy of photoacoustic images.

  本发明提供了一种两用光声断层成像（PAT）/超声造影剂，包括：(a) 内含气体和卟啉的微气泡；(b) 结合在微气泡表面并含有药物的纳米颗粒。本发明的造影剂可用于超声诊断和光声图像诊断，并能显著提高光声图像的准确性。