(9Z)-9-octadecenoate-(2’S)-2’,3’-dihydroxypropyl ester | 34487-30-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (9Z)-9-octadecenoate-(2’S)-2’,3’-dihydroxypropyl ester
• 英文别名: 9-octadecenoic acid-2′,3′-dihydroxypropylester；(S)-2,3-dihydroxypropyl (Z)-9-octadecenoate；(9Z)-2,3-dihydroxypropyl octadec-9-enoate；1-O-cis-octadec-9-enoyl-sn-glycerol；1-oleoyl-sn-glycerol；(S)-1-monoolein；(2s)-2,3-Dihydroxypropyl (9z)-Octadec-9-Enoate；[(2S)-2,3-dihydroxypropyl] (Z)-octadec-9-enoate
• CAS: 34487-30-4
• 化学式: C₂₁H₄₀O₄
• 分子量: 356.546
• InChiKey: RZRNAYUHWVFMIP-QJRAZLAKSA-N

物化性质

• 沸点：
  483.3±35.0 °C(Predicted)
• 密度：
  0.969±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  25
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9Z)-9-octadecenoate-(2’S)-2’,3’-dihydroxypropyl ester 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-O-tert-butyldimethylsilanyl-1-O-cis-octadec-9-enoyl-sn-glycerol
  参考文献：
  名称：

  Synthesis and evaluation of immunostimulant plasmalogen lysophosphatidylethanolamine and analogues for natural killer T cells

  摘要：

  Plasmalogen lysophosphatidylethanolamine (pLPE) had been identified as a self antigen for natural killer T cells (NKT cells). It is very important in the development, maturation and activation of NKT cells in thymus. Besides, pLPE is a novel type of antigen for NKT cells. To evaluate the structure-activity relationship (SAR) of this new antigen, pLPE and its analogues referred to different aliphatic chains and linkages at the sn-1 position of the glycerol backbone were synthesized, and the biological activities of these analogues was characterized. It is discovered that the linkages between phosphate and lipid moiety are not important for the antigens' activities. The pLPE analogues 1, 3, 4, 7 and 9, which have additional double bonds on lipid parts, were identified as new NKT agonists. Moreover, the analogues 4, 7 and 9 were discovered as potent Th2 activators for NKT cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.012
• 作为产物：
  描述：

  油酰氯 在 吡啶 、 4-二甲氨基吡啶 、 水 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (9Z)-9-octadecenoate-(2’S)-2’,3’-dihydroxypropyl ester
  参考文献：
  名称：

  信息素合成。第253部分：果蝇雄性果蝇甘油三酸酯的外消旋物和对映体的合成，特别着重于对映体纯的1-甘油单酸酯的制备

  摘要：

  蝇果蝇的果蝇的外消旋体和对映异构体（2，3-丙酮甘油的外消旋体和对映异构体）通过三个步骤合成了甘油三酸酯1a – e（果蝇的果蝇的棕榈酸，棕榈油酸，硬脂酸，油酸和亚油酸的2,3-二聚二羟甲氧基丙基酯）。（2）通过1-甘油单酸酯4a - e衍生自上述脂肪酸。建立了制备对映体纯的1-甘油单酸酯4a - e的适当条件，并通过相应的bis-（R）-MTPA酯的NMR分析确定了它们的对映体纯度。

  DOI：

  10.1016/j.tet.2012.07.086

文献信息

• Regioselective and stereospecific acylation across oxirane- and silyloxy systems as a novel strategy to the synthesis of enantiomerically pure mono-, di- and triglycerides
  作者：Stephan D. Stamatov、Jacek Stawinski

  DOI：10.1039/b713246h

  日期：——

  acyl residue at the central carbon of the silylated synthons with a subsequent Et(3)N.3HF-promoted, direct trichloroacetylation across the siloxy system by trichloroacetic anhydride (TCAA), followed by cleavage of the trichloroacetyl group, affords the respective 1,2(2,3)-diacyl- or 1(3)-O-alkyl-2-acyl-sn-glycerols. Alternatively, a reaction sequence involving: (i) attachment of a trichloroacetyl fragment

  三氟乙酸催化带有三氟乙酸酐（TFAA）的带有烯丙基酰基或烷基官能团的缩水甘油基衍生物的环氧乙烷环的开环，可有效进入构型均质的1（3）-酰基-或1（3）-O-烷基-sn -甘油。在这些关键中间体的末端位置选择性引入叔丁基二甲基甲硅烷基-（TBDMS）或三异丙基甲硅烷基-（TIPS）瞬态保护可确保1（3）-酰基-或1（3）-O-烷基-3（1）- O-TBDMS（或TIPS）-sn-甘油作为1,2（2,3）-二酰基-，1（3）-O-烷基-2-酰基-和1,3-二酰基-sn-的一般双功能前体甘油和三酯等排体。通过三氯乙酸酐（TCAA）在甲硅烷基化的合成子的中央碳原子上引入必要的酰基残基，并随后进行Et（3）N.3HF促进的，直接的三氯乙酰化作用穿过硅烷氧基体系 然后裂解三氯乙酰基，得到各自的1,2（2,3）-二酰基-或1（3）-O-烷基-2-酰基-sn-甘油。可选择地，反应序列包括：（i）三氯乙酰基片段连接在单甲硅烷基化甘油酯的立体C
• [EN] TLR7/8 AGONISTS AND LIPOSOME COMPOSITIONS<br/>[FR] AGONISTES DE TLR7/8 ET COMPOSITIONS LIPOSOMALES
  申请人：TORQUE THERAPEUTICS INC

  公开号：WO2020023680A1

  公开（公告）日：2020-01-30

  The present disclosure relates to a method of loading a toll like receptor (TLR)7/8 agonist into a liposome using remote loading and a kit of parts suitable for the loading of a TLR7/8 agonist into a liposome by said method. The present disclosure further relates to a liposome comprising a salt of a TLR7/8 agonist in the liposome interior and to the use of said liposome for stimulation of an immune response and/or treatment of a clinical condition. Finally, the present disclosure relates to a TLR7/8 agonist which is suitable for being remotely loaded into a liposome.

  本公开涉及一种利用远程加载的方法将调节剂（TLR）7/8激动剂装载到脂质体中，以及适用于通过该方法将TLR7/8激动剂装载到脂质体的部件套件。本公开进一步涉及包含TLR7/8激动剂盐的脂质体，并且利用该脂质体用于刺激免疫反应和/或治疗临床疾病。最后，本公开涉及一种适合远程装载到脂质体中的TLR7/8激动剂。
• Stereochemistry, lipid length and branching influences Mincle agonist activity of monoacylglycerides
  作者：Ayesha Khan、Chriselle D. Braganza、Kristel Kodar、Mattie S. M. Timmer、Bridget L. Stocker

  DOI：10.1039/c9ob02302j

  日期：——

  than trehalose dibehenate (TDB), the prototypical Mincle agonist. Across the compound classes, the activity of the sn-1 substituted isomers was greater than the sn-3 counterparts. None of the representative compounds were cytotoxic, thus mitigating cytotoxicity as a potential mediator of cellular activity. Taken together, 6h (sn-1, iC26+1), 8a (sn-1, C32) and 8b (sn-3, C32) exhibited the best immunostimulatory

  在这里，我们报道了一系列对映体纯的线性，异支化和α支化单酰基甘油酯（MAGs）的合成，总收率为63-72％。探索了使用NFAT-GFP报告基因细胞通过人巨噬细胞诱导型C型凝集素（hMincle）发出信号的能力，以及化合物激活人单核细胞的能力。从这些研究中，人单核细胞的Mincle激活和白介素8（IL-8）的产生需要酰基链长度≥C22的MAG。此外，与线性MAG相比，异支MAG导致更明显的免疫反应，而含有C-32酰基链的α支MAG则比典型的Mincle激动剂海藻糖二山hen酸酯（TDB）活化细胞的程度更高。在整个复合类别中，sn的活动-1个取代的异构体大于sn -3对应的异构体。代表性化合物均无细胞毒性，因此可减轻细胞毒性，将其作为细胞活性的潜在介质。两者合计，6h（sn -1，iC26 + 1），8a（sn -1，C32）和8b（sn -3，C32）表现出最佳的免疫刺激特性，因此具有作为疫苗佐剂的潜力。
• Synthesis and hydrolytic stability of cyclic phosphatidic acids: implications for synthetic- and proto-cell studies
  作者：Veronica Egas Ortuno、Sunil Pulletikurti、Kollery S. Veena、Ramanarayanan Krishnamurthy

  DOI：10.1039/d2cc00292b

  日期：——

  Cyclic phosphatidic acids (cPAs) are bioactive compounds with therapuetic potential, but are in short supply. We describe a robust synthesis of cPAs employing an efficient cyclophosphorylation procedure and report on their hydrolytic properties – which should facilitate the study of their biological properties and as plausible proto- and synthetic-cell components.

  环磷脂酸 (cPA) 是具有治疗潜力的生物活性化合物，但供不应求。我们描述了采用有效的环磷酸化程序的 cPA 的稳健合成，并报告了它们的水解特性——这应该有助于研究它们的生物学特性以及作为合理的原始细胞和合成细胞成分。
• A novel acylglycerol kinase that produces lysophosphatidic acid modulates cross talk with EGFR in prostate cancer cells
  作者：Meryem Bektas、Shawn G. Payne、Hong Liu、Sravan Goparaju、Sheldon Milstien、Sarah Spiegel

  DOI：10.1083/jcb.200407123

  日期：2005.6.6

  The bioactive phospholipids, lysophosphatidic acid (LPA) and phosphatidic acid (PA), regulate pivotal processes related to the pathogenesis of cancer. Here, we report characterization of a novel lipid kinase, designated acylglycerol kinase (AGK), that phosphorylates monoacylglycerol and diacylglycerol to form LPA and PA, respectively. Confocal microscopy and subcellular fractionation suggest that AGK is localized to the mitochondria. AGK expression was up-regulated in prostate cancers compared with normal prostate tissues from the same patient. Expression of AGK in PC-3 prostate cancer cells markedly increased formation and secretion of LPA. This increase resulted in concomitant transactivation of the EGF receptor and sustained activation of extracellular signal related kinase (ERK) 1/2, culminating in enhanced cell proliferation. AGK expression also increased migratory responses. Conversely, down-regulating expression of endogenous AGK inhibited EGF- but not LPA-induced ERK1/2 activation and progression through the S phase of the cell cycle. Hence, AGK can amplify EGF signaling pathways and may play an important role in the pathophysiology of prostate cancer.

  生物活性磷脂，溶血磷脂酸（LPA）和磷脂酸（PA），调节与癌症发病相关的关键过程。在这里，我们报告了一个新型脂肪激酶的特性，称为酰基甘油激酶（AGK），它磷酸化单酰基甘油和二酰基甘油形成LPA和PA。共聚焦显微镜和亚细胞分离表明AGK定位于线粒体。与同一患者的正常前列腺组织相比，AGK表达在前列腺癌中上调。在PC-3前列腺癌细胞中表达AGK显著增加了LPA的形成和分泌。这种增加导致EGF受体的同时转录活化和细胞外信号相关激酶（ERK）1/2持续活化，最终增强了细胞增殖。AGK表达也增加了细胞的迁移反应。相反，下调内源性AGK的表达抑制了EGF诱导的ERK1/2活化和细胞周期S期的进展，但不影响LPA诱导的作用。因此，AGK可以放大EGF信号通路，并可能在前列腺癌的病理生理学中发挥重要作用。