sn-2,3-dioctanoylglycerol | 113973-38-9

• 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: sn-2,3-dioctanoylglycerol
• 英文别名: (R)-1,2-dioctoylglycerol；DOG；2,3-Dioctanoylglycerol；[(2R)-3-hydroxy-2-octanoyloxypropyl] octanoate
• CAS: 113973-38-9
• 化学式: C₁₉H₃₆O₅
• 分子量: 344.492
• InChiKey: ZQBULZYTDGUSSK-QGZVFWFLSA-N

物化性质

• 沸点：
  429.1±12.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  sn-2,3-dioctanoylglycerol 在 palladium on activated charcoal 四氮唑 、 氢气 、 双氧水 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 Octanoic acid (S)-1-octanoyloxymethyl-2-phosphonooxy-ethyl ester
  参考文献：
  名称：

  作为溶血磷脂酸受体配体的第二代磷脂酸衍生物的合成和药理评价。

  摘要：

  短链磷脂酸衍生物，焦磷酸二辛酯甘油酯（DGPP 8：0，1）和磷脂酸8：0（PA 8：0，2）先前被确定为亚型选择性LPA（1）和LPA（3）受体拮抗剂。最近，我们报道了在一系列脂肪醇磷酸酯（FAP）中用硫代磷酸酯取代磷酸根基可以改善LPA GPCR的激动剂和拮抗剂活性。在这里，我们报告PA 8：0类似物的立体异构体的合成及其在LPA GPCR，PPARgamma和ATX的生物学评估。结果表明，LPA受体与甘油骨架修饰的配体立体选择性地相互作用。我们观察到由二辛基PA 8：0化合物产生的完全立体定向反应，其中（R）异构体是激动剂，（S）异构体是LPA GPCR的拮抗剂。从这个系列中 我们将化合物13b确定为最有效的LPA（3）受体亚型选择性激动剂（EC（50）= 3 nM），将8b确定为有效和选择性的LPA（3）受体拮抗剂（K（i）= 5 nM）和ATX抑制剂（IC（50）= 600 nM

  DOI：

  10.1016/j.bmcl.2005.10.031
• 作为产物：
  描述：

  [(2R)-3-[(4-methoxyphenyl)methoxy]-2-octanoyloxypropyl] octanoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 sn-2,3-dioctanoylglycerol
  参考文献：
  名称：

  Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism

  摘要：

  The stereochemistry of glycerophospholipids (GPLs) has been of interest for its roles in the evolution of life and in their biological activity. However, because of their structural complexity, no convenient method to determine their configuration has been reported. In this work, through the first systematic application of vibrational circular dichroism (VCD) spectroscopy to various diacylated GPLs, we have revealed that their chirality can be assigned by the sign of a VCD exciton couplet generated by the interaction of two carbonyl groups. This paper also presents spectroscopic evidence for the stereochemistry of GPLs isolated from bacteria, eukaryotes, and mitochondria.

  DOI：

  10.1021/jacs.5b05832

文献信息

• Acetal phosphate-derived LPA mimics, PPARgamma activators, and autotaxin inhibitors
  申请人：Miller D. Duane

  公开号：US20060270634A1

  公开（公告）日：2006-11-30

  Disclosed are compositions that modulate the effects of extracellular LPA receptors, the intracellular PPARγ receptor, and autotaxin, and methods for their use.

  揭示了调节细胞外LPA受体、细胞内PPARγ受体和自体脂肪酶效应的组合物，以及它们的使用方法。
• Streamlined Synthesis of Phosphatidylinositol (PI), PI3P, PI3,5P₂, and Deoxygenated Analogues as Potential Biological Probes
  作者：Yingju Xu、Bianca R. Sculimbrene、Scott J. Miller

  DOI：10.1021/jo060702s

  日期：2006.6.1

  Highly direct total syntheses of phosphatidylinositol (PI), phosphatidylinositol-3-phosphate (PI3P), phosphatidylinositol-3,5-bisphosphate (PI3,5P2), and a range of deoxygenated versions are reported. Each synthesis is carried out to deliver the target in optically pure form. The key step for each synthesis is a catalytic asymmetric phosphorylation reaction that affects desymmetrization of an appropriate

  据报道，磷脂酰肌醇（PI），磷脂酰肌醇-3-磷酸酯（PI3P），磷脂酰肌醇-3,5-双磷酸酯（PI3,5P 2）和一系列脱氧形式的高度直接的全合成。进行每个合成以递送光学纯形式的靶标。对于每个合成中的关键步骤是催化不对称磷酸化反应，影响适当的desymmetrization肌醇-肌醇的前体。然后采用通用前体的面向多样性的策略对每种目标化合物进行精细加工。除三种天然产物外，还报道了几种其他简化的脱氧PI类似物的总合成方法。这些合成为这些膜相关信号分子的极性头基/生物靶标相互作用的高精度生物学研究奠定了基础。
• Stereoselective hydrolysis of triglycerides by animal and microbial lipases
  作者：Ewa Rogalska、Claire Cudrey、Francine Ferrato、Robert Verger

  DOI：10.1002/chir.530050106

  日期：——

  (Rogalska et al., J. Biol. Chem. 256:20271-20276, 1990). Hydrolysis of the sn-2 ester group is catalysed by very few lipases and only Candida antarctica A shows a clear preference for this position. Most of the lipases investigated (12 with trioctanoin and 16 with triolein) showed a preference for the sn-1 position. Using trioctanoin as substrate we observed a total stereoselectivity for position sn-1 with

  在本文中，对动物和微生物来源的25种脂肪酶对均相前手性甘油三酸酯的立体选择性进行了研究。根据底物的脂肪酰基链长度，所有测试的脂肪酶均会催化三辛酸和三油酸酯中化学相似但空间上不等价的酯基团的水解，这些酯基团具有不同的立体偏斜度（Rogalska等人，J.Biol.Chem.256： 20271-20276，1990）。很少的脂肪酶催化sn-2酯基团的水解，只有南极假丝酵母A明显偏爱该位置。研究的大多数脂肪酶（含三辛酸的脂酶为12个，含三油酸的脂酶为16个）显示对sn-1位置的偏爱。使用三辛酸为底物，我们观察到了假单胞菌属sp的位置sn-1的总立体选择性。和铜绿假单胞菌，以及南极假丝酵母B的sn-3位置。以三油精为底物的情况并非如此。在本文研究的23种脂肪酶和先前描述的其他两种脂肪酶（Rogalska等人，J.Biol.Chem.256：20271-20276，1990）中，用三辛酸比用三油酸
• Studies on the substrate specificity of purified human milk lipoprotein lipase
  作者：C. ‐S. Wang、A. Kuksis、F. Manganaro

  DOI：10.1007/bf02534942

  日期：1982.4

  The fatty acid specificity of purified human milk lipoprotein lipase was studied using the C₁₈ to C₅₄ (total acyl carbon number) saturated and the C₅₄ mono‐, di‐ and triunsaturated monoacid triacylglycerols. Kinetic determinations indicated that the medium‐chain triacylglycerols were better substrates than long‐ or very short‐chain saturated triacylglycerols. The unsaturated triacylglycerols were hydrolyzed at rates comparable to that of tricaprylin with triolein having the highest rate of hydrolysis of the unsaturated species tested. The enzyme attacked the primary ester bond much more readily than the secondary ester bond. The purified human milk lipoprotein lipase showed a preferential stereospecific lipolysis of thesn‐1‐position of the triacylglycerol molecule.

  摘要 使用 C18 至 C54（酰基总碳数）饱和和 C54 单酸、双酸和三酸三酰甘油研究了纯化人乳脂蛋白脂肪酶的脂肪酸特异性。动力学测定表明，与长链或极短链饱和三酰甘油相比，中链三酰甘油是更好的底物。不饱和三酰甘油的水解速度与三碳甘油酯的水解速度相当，其中三烯甘油酯的水解速度在所测试的不饱和三酰甘油酯中最高。该酶攻击一级酯键的速度比攻击二级酯键的速度快得多。纯化的人乳脂蛋白脂肪酶对三酰基甘油分子的sn-1位显示出优先的立体特异性脂肪分解作用。
• Asymmetric Total Synthesis of Phosphatidylinositol 3-Phosphate and 4-Phosphate Derivatives
  作者：Jian Chen、Li Feng、Glenn D. Prestwich

  DOI：10.1021/jo980501r

  日期：1998.9.1

  New asymmetric syntheses of phosphatidylinositol 3-phosphate (PtdIns(3)P) and phosphatidylinositol 4-phosphate (PtdIns(4)P) derivatives are described. Key intermediates were used to prepare diacylglyceryl moieties with dibutyryl, dioctanoyl, and dihexadecanoyl chains. In addition, a modified route provided PtdIns(3)P and PtdIns(4)P triesters with P-1-linked aminopropyl groups for preparation of affinity probes. The synthesis of the inosityl precursor employed a dibutyltin oxide-mediated p-methoxybenzyl (PMB) etherification to give either the 2-PMB- or the 3-PMB-protected glucopyranosides. The Ferrier rearrangement was used to convert suitably protected glucose derivatives to enantiomerically pure, differentially protected D-myo-inositol key intermediates. A versatile phosphoramidite reagent was employed to allow synthesis of PtdInsP(n), derivatives with diacylglyceryl moieties of different chain lengths.