1-棕榈酰-2-棕榈油酰基-Sn-甘油-3-磷酰胆碱 | 53595-24-7

• 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-棕榈油酰基-Sn-甘油-3-磷酰胆碱
• 英文名称: 1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine
• 英文别名: [(2R)-3-hexadecanoyloxy-2-[(Z)-hexadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 53595-24-7
• 化学式: C40H78NO8P
• 分子量: 732.0
• InChiKey: QIBZFHLFHCIUOT-NPBIGWJUSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  50
• 可旋转键数：
  39
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine 、 溶血磷脂酰胆碱(鸡蛋) 生成 lysoPC(16:1(9Z)) 、 1-棕榈酰-2-棕榈油酰基-Sn-甘油-3-磷酰胆碱
  参考文献：
  名称：

  线粒体心磷脂分子种类的形成。1. 一种在多种磷脂种类的 sn-1 和 sn-2 位置之间穿梭脂肪酸的新型转酰基机制。

  摘要：

  线粒体心磷脂对其酰基进行了广泛的重塑，以产生均匀取代的物种，例如四亚油酰心磷脂，但这种重塑的机制尚未阐明，除了它需要 tafazzin 之外。在这里，我们显示纯化的重组果蝇 tafazzin 通过正向和反向转移的组合在心磷脂和磷脂酰胆碱之间交换酰基。在没有磷脂酶 A(2) 的情况下，酰基交换是可能的，因为它只需要微量的溶血磷脂。我们表明纯化的 tafazzin 与各种磷脂类以及 sn-1 和 sn-2 位置的各种酰基反应。Sf9 昆虫细胞中的表达研究表明，tafazzin 对心磷脂种类的影响取决于细胞环境，而不是酶底物特异性。我们的数据表明，tafazzin 催化磷脂之间的一般酰基交换，这提出了一个问题，即心磷脂中的模式形成是否是多种磷脂物种之间酰基平衡分布的结果。

  DOI：

  10.1016/j.bbalip.2009.01.004

文献信息

• <i>Drosophila</i>Lysophospholipid Acyltransferases Are Specifically Required for Germ Cell Development
  作者：Josefa Steinhauer、Miguel A. Gijón、Wayne R. Riekhof、Dennis R. Voelker、Robert C. Murphy、Jessica E. Treisman

  DOI：10.1091/mbc.e09-05-0382

  日期：2009.12.15

  Enzymes of the membrane-bound O-acyltransferase (MBOAT) family add fatty acyl chains to a diverse range of protein and lipid substrates. A chromosomal translocation disrupting human MBOAT1 results in a novel syndrome characterized by male sterility and brachydactyly. We have found that the Drosophila homologues of MBOAT1, Oysgedart (Oys), Nessy (Nes), and Farjavit (Frj), are lysophospholipid acyltransferases. When expressed in yeast, these MBOATs esterify specific lysophospholipids preferentially with unsaturated fatty acids. Generating null mutations for each gene allowed us to identify redundant functions for Oys and Nes in two distinct aspects of Drosophila germ cell development. Embryos lacking both oys and nes show defects in the ability of germ cells to migrate into the mesoderm, a process guided by lipid signals. In addition, oys nes double mutant adult males are sterile due to specific defects in spermatid individualization. oys nes mutant testes, as well as single, double, and triple mutant whole adult animals, show an increase in the saturated fatty acid content of several phospholipid species. Our findings suggest that lysophospholipid acyltransferase activity is essential for germline development and could provide a mechanistic explanation for the etiology of the human MBOAT1 mutation.

  膜结合O-酰转移酶（MBOAT）家族的酶可以向多种蛋白质和脂质底物中加入脂肪酰基。破坏人类MBOAT1的染色体易位导致一种新的综合症，其特征为男性不育和短指。我们发现果蝇MBOAT1的同源物Oysgedart（Oys）、Nessy（Nes）和Farjavit（Frj）是溶解磷脂酰基转移酶。当在酵母中表达这些MBOAT时，它们会选择性地酯化特定的溶解磷脂酰基，特别是不饱和脂肪酸。通过产生每个基因的空突变，我们确定了Oys和Nes在果蝇生殖细胞发育的两个不同方面中具有冗余功能。缺乏oys和nes的胚胎显示出生殖细胞进入中胚层的能力受到缺陷，这是由脂质信号引导的过程。此外，oys nes双突变体成年雄性不育，由于精子个体化的特定缺陷。oys nes突变体睾丸以及单个、双重和三重突变体的整个成年动物显示出多种磷脂酰基中饱和脂肪酸含量的增加。我们的发现表明，溶解磷脂酰基转移酶活性对生殖细胞发育至关重要，并可以为人类MBOAT1突变的病因提供机制解释。
• Role of Acyl Chain Composition of Phosphatidylcholine in Tafazzin-Mediated Remodeling of Cardiolipin in Liposomes
  作者：Masato Abe、Yoshiki Sawada、Shinpei Uno、Shuhei Chigasaki、Masahide Oku、Yasuyoshi Sakai、Hideto Miyoshi

  DOI：10.1021/acs.biochem.7b00941

  日期：2017.11.28

  Remodeling of the acyl chain compositions of cardiolipin (CL) species by the transacylase tafazzin is an important process for maintaining optimal mitochondrial functions. The results of mechanistic studies on the tafazzin-mediated transacylation from phosphatidylcholine (PC) to monolyso-CL (MLCL) in artificial lipid membranes are controversial. The present study investigated the role of the acyl chain composition of PC in the Saccharomyces cerevisiae tafazzin-mediated remodeling of CL by examining the structural factors responsible for the superior acyl donor ability of dipalmitoleoyl (16:1) PC over dipalmitoyl (16:0) PC. To this end, we synthesized systematic derivatives of dipalmitoleoyl PC; for example, the location of the cis double bond was migrated from the Δ9-position toward either end of the acyl chains (the Δ5- or Δ13-position), the cis double bond in the sn-1 or sn-2 position or both, was changed to a trans form, and palmitoleoyl and palmitoyl groups were exchanged in the sn-1 and sn-2 positions, maintaining similar PC fluidities. Analyses of the tafazzin-mediated transacylation from these PCs to sn-2′-MLCL(18:1-18:1/18:1-OH) in the liposomal membrane revealed that tafazzin strictly discriminates the molecular configuration of the acyl chains of PCs, including their glycerol positions (sn-1 or sn-2); however, the effects of PC fluidity on the reaction may not be neglected. On the basis of the findings described herein, we discuss the relevance of the so-called thermodynamic remodeling hypothesis that presumes no acyl selectivity of tafazzin.

  通过转酰基酶塔法津重塑心磷脂（CL）的酰基链组成是维持线粒体最佳功能的重要过程。关于人工脂质膜中塔法津介导的磷脂酰胆碱（PC）向单溶酶-CL（MLCL）转酰基化的机理研究结果存在争议。本研究通过检测双棕榈酰（16:1）PC比双棕榈酰（16:0）PC具有更优越的酰基供体能力的结构因素，研究了PC的酰基链组成在酿酒酵母塔法津介导的CL重塑中的作用。为此，我们合成了双棕榈酰PC的系统衍生物；例如，顺式双键的位置从Δ9位向酰基链的两端（Δ5位或Δ13位）移动，sn-1或sn-2位或两者的顺式双键变为反式，并在sn-1和sn-2位交换棕榈酰基和棕榈酰基，以保持相似的PC流动性。对脂质体膜中塔法津介导的从这些PC向sn-2′-MLCL（18:1-18:1/18:1-OH）的转酰基化分析表明，塔法津严格区分PC的酰基链的分子构型，包括其甘油位置（sn-
• Lysophospholipid Acyltransferases and Arachidonate Recycling in Human Neutrophils
  作者：Miguel A. Gijón、Wayne R. Riekhof、Simona Zarini、Robert C. Murphy、Dennis R. Voelker

  DOI：10.1074/jbc.m806194200

  日期：2008.10

  The cycle of deacylation and reacylation of phospholipids plays a critical role in regulating availability of arachidonic acid for eicosanoid production. The major yeast lysophospholipid acyltransferase, Ale1p, is related to mammalian membrane-bound O-acyltransferase (MBOAT) proteins. We expressed four human MBOATs in yeast strains lacking Ale1p and studied their acyl-CoA and lysophospholipid specificities using novel mass spectrometry-based enzyme assays. MBOAT1 is a lysophosphatidylserine (lyso-PS) acyltransferase with preference for oleoyl-CoA. MBOAT2 also prefers oleoyl-CoA, using lysophosphatidic acid and lysophosphatidylethanolamine as acyl acceptors. MBOAT5 prefers lysophosphatidylcholine and lyso-PS to incorporate linoleoyl and arachidonoyl chains. MBOAT7 is a lysophosphatidylinositol acyltransferase with remarkable specificity for arachidonoyl-CoA. MBOAT5 and MBOAT7 are particularly susceptible to inhibition by thimerosal. Human neutrophils express mRNA for these four enzymes, and neutrophil microsomes incorporate arachidonoyl chains into phosphatidylinositol, phosphatidylcholine, PS, and phosphatidylethanolamine in a thimerosal-sensitive manner. These results strongly implicate MBOAT5 and MBOAT7 in arachidonate recycling, thus regulating free arachidonic acid levels and leukotriene synthesis in neutrophils.
• Identification of a Novel Lysophospholipid Acyltransferase in Saccharomyces cerevisiae
  作者：Shilpa Jain、NaTaza Stanford、Neha Bhagwat、Brian Seiler、Michael Costanzo、Charles Boone、Peter Oelkers

  DOI：10.1074/jbc.m706326200

  日期：2007.10

  The incorporation of unsaturated acyl chains into phospholipids during de novo synthesis is primarily mediated by the 1-acyl-sn-glycerol-3-phosphate acyltransferase reaction. In Saccharomyces cerevisiae, Slc1 has been shown to mediate this reaction, but distinct activity remains after its removal from the genome. To identify the enzyme that mediates the remaining activity, we performed synthetic genetic array analysis using a slc1 Delta strain. One of the genes identified by the screen, LPT1, was found to encode for an acyltransferase that uses a variety of lysophospholipid species, including 1-acyl-sn-glycerol-3-phosphate. Deletion of LPT1 had a minimal effect on 1-acyl-sn-glycerol-3-phosphate acyltransferase activity, but overexpression increased activity 7-fold. Deletion of LPT1 abrogated the esterification of other lysophospholipids, and overexpression increased lysophosphatidylcholine acyltransferase activity 7-fold. The majority of this activity co-purified with microsomes. To test the putative role for this enzyme in selectively incorporating unsaturated acyl chains into phospholipids in vitro, substrate concentration series experiments were performed with the four acyl-CoA species commonly found in yeast. Although the saturated palmitoyl-CoA and stearoyl-CoA showed a lower apparent Km, the monounsaturated palmitoleoyl-CoA and oleoyl-CoA showed a higher apparent V-max. Arachidonyl-CoA, although not abundant in yeast, also had a high apparent V-max. Pulse- labeling of lpt1 Delta strains showed a 30% reduction in [H-3] oleate incorporation into phosphatidylcholine only. Therefore, Lpt1p, a member of the membrane-bound o-acyltransferase gene family, seems to work in conjunction with Slc1 to mediate the incorporation of unsaturated acyl chains into the sn-2 position of phospholipids.
• Formation of molecular species of mitochondrial cardiolipin. 1. A novel transacylation mechanism to shuttle fatty acids between sn-1 and sn-2 positions of multiple phospholipid species
  作者：Ashim Malhotra、Yang Xu、Mindong Ren、Michael Schlame

  DOI：10.1016/j.bbalip.2009.01.004

  日期：2009.4

  of phospholipase A(2) because it requires only trace amounts of lysophospholipids. We show that purified tafazzin reacts with various phospholipid classes and with various acyl groups both in sn-1 and sn-2 position. Expression studies in Sf9 insect cells suggest that the effect of tafazzin on cardiolipin species is dependent on the cellular environment and not on enzymatic substrate specificity. Our

  线粒体心磷脂对其酰基进行了广泛的重塑，以产生均匀取代的物种，例如四亚油酰心磷脂，但这种重塑的机制尚未阐明，除了它需要 tafazzin 之外。在这里，我们显示纯化的重组果蝇 tafazzin 通过正向和反向转移的组合在心磷脂和磷脂酰胆碱之间交换酰基。在没有磷脂酶 A(2) 的情况下，酰基交换是可能的，因为它只需要微量的溶血磷脂。我们表明纯化的 tafazzin 与各种磷脂类以及 sn-1 和 sn-2 位置的各种酰基反应。Sf9 昆虫细胞中的表达研究表明，tafazzin 对心磷脂种类的影响取决于细胞环境，而不是酶底物特异性。我们的数据表明，tafazzin 催化磷脂之间的一般酰基交换，这提出了一个问题，即心磷脂中的模式形成是否是多种磷脂物种之间酰基平衡分布的结果。