(R)-2-(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)-3-(oleoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate | 17041-44-0

• 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: (R)-2-(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)-3-(oleoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate
• 英文别名: L-(+)-α(α'Oleoyl-β-linoleoyl)glycerylphosphorylcholin；1-(9Z-octadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine；[(2R)-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxy-3-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 17041-44-0
• 化学式: C₄₄H₈₂NO₈P
• 分子量: 784.111
• InChiKey: GDWULUGDXGHJIJ-VJHNMZKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.1
• 重原子数：
  54
• 可旋转键数：
  41
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  linoleoyl-CoA(4-) 、 (2R)-2-羟基-3-[(9Z)-9-十八碳烯酰基氧基]丙基 2-(三甲基铵基)乙基磷酸酯 生成 (R)-2-(((9Z,12Z)-octadeca-9,12-dienoyl)oxy)-3-(oleoyloxy)propyl (2-(trimethylammonio)ethyl) phosphate 、 coenzyme A
  参考文献：
  名称：

  Lysophospholipid Acyltransferases and Arachidonate Recycling in Human Neutrophils

  摘要：

  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.

  DOI：

  10.1074/jbc.m806194200

文献信息

• 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。
• Phospholipid compositions
  申请人：MACHAVERT PHARMACEUTICALS LLC

  公开号：US10493086B2

  公开（公告）日：2019-12-03

  Compositions involving a modified egg yolk extract for use as an effective anti-cancer agent are described. The modified egg yolk extract involves specific fractions of phosphatidylcholines and sphingomyelins modified and produced from a chemical synthesis applied to the extract that produce a beneficial effect on the inhibition of cancerous cell growth. Methods of administering these compositions are also described.

  本研究描述了改性蛋黄提取物作为有效抗癌剂的成分。改良的蛋黄提取物包括经改良的磷脂酰胆碱和鞘磷脂的特定组分，这些组分是通过对提取物进行化学合成而产生的，对抑制癌细胞生长产生有益的作用。此外，还介绍了施用这些组合物的方法。
• Peptides with antioxidant and antimicrobial properties
  申请人：——

  公开号：US20040037781A1

  公开（公告）日：2004-02-26

  Methods of treating conditions associated with lipid oxidation or microbial proliferation include the step of administering a composition comprising a pharmacologically effective amount of an antioxidant or antimicrobial lung surfactant protein compound. Peptides derived from lung surfactant protein compounds possess lipid oxidation inhibiting and/or antimicrobial properties.

  治疗与脂质氧化或微生物增殖相关的疾病的方法包括施用一种组合物，该组合物包含药理有效量的抗氧化剂或抗菌剂肺表面活性蛋白化合物。从肺表面活性蛋白化合物中提取的肽具有抑制脂质氧化和/或抗菌的特性。
• Investigations in the field of complex lipids
  作者：V. I. Shvets、V. A. Klopova、N. A. Preobrazhenskii

  DOI：10.1007/bf00564083

  日期：1966.7
• Plant Acyl-CoA:Lysophosphatidylcholine Acyltransferases (LPCATs) Have Different Specificities in Their Forward and Reverse Reactions
  作者：Ida Lager、Jenny Lindberg Yilmaz、Xue-Rong Zhou、Katarzyna Jasieniecka、Michael Kazachkov、Peng Wang、Jitao Zou、Randall Weselake、Mark A. Smith、Shen Bayon、John M. Dyer、Jay M. Shockey、Ernst Heinz、Allan Green、Antoni Banas、Sten Stymne

  DOI：10.1074/jbc.m113.521815

  日期：2013.12

  Acyl-CoA:lysophosphatidylcholine acyltransferase (LPCAT) enzymes have central roles in acyl editing of phosphatidylcholine (PC). Plant LPCAT genes were expressed in yeast and characterized biochemically in microsomal preparations of the cells. Specificities for different acyl-CoAs were similar for seven LPCATs from five different species, including species accumulating hydroxylated acyl groups in their seed oil, with a preference for C-18-unsaturated acyl-CoA and low activity with palmitoyl-CoA and ricinoleoyl (12-hydroxyoctadec-9-enoyl)-CoA. We showed that Arabidopsis LPCAT1 and LPCAT2 enzymes catalyzed the acylation and de-acylation of both sn positions of PC, with a preference for the sn-2 position. When acyl specificities of the Arabidopsis LPCATs were measured in the reverse reaction, sn-2-bound oleoyl, linoleoyl, and linolenoyl groups from PC were transferred to acyl-CoA to a similar extent. However, a ricinoleoyl group at the sn-2-position of PC was removed 4-6-fold faster than an oleoyl group in the reverse reaction, despite poor utilization in the forward reaction. The data presented, taken together with earlier published reports on in vivo lipid metabolism, support the hypothesis that plant LPCAT enzymes play an important role in regulating the acyl-CoA composition in plant cells by transferring polyunsaturated and hydroxy fatty acids produced on PC directly to the acyl-CoA pool for further metabolism or catabolism.