十四烷酸2,3-二羟丙基酯 | 86195-50-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 十四烷酸2,3-二羟丙基酯
• 英文名称: tetradecanoic acid 2,3-dihydroxypropyl ester
• 英文别名: 1-tetradecanoyl-sn-glycerol；1-myristoyl-sn-glycerol；[(2S)-2,3-dihydroxypropyl] tetradecanoate
• CAS: 86195-50-8
• 化学式: C₁₇H₃₄O₄
• 分子量: 302.455
• InChiKey: DCBSHORRWZKAKO-INIZCTEOSA-N

物化性质

• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  十四烷酸2,3-二羟丙基酯 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 氟化氢吡啶 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 83.25h， 生成 1-tetradecanoic acid 3-({[(N,N,N-trimethylammonio)ethoxy]hydroxyphosphoryl}oxy)-2-({12-[2-(4-diazocyclohexa-2,5-dienonyl)methylenoxy]dodecanoyl}oxy)propyl ester
  参考文献：
  名称：

  Synthesis and Properties of Photoactivatable Phospholipid Derivatives Designed To Probe the Membrane-Associate Domains of Proteins

  摘要：

  The total syntheses of photoactivatable phospholipidic probes 1 and 2 are described. These probes contain either an aryldiazonium function at their polar head (probes la and Ib) or an diazocyclohexadienonyl group attached to the end of one fatty acid side chain (probe 2) and have been designed to probe the lipid/water interface and the hydrophobic core of the membrane, respectively. The synthetic schemes include the possibility of incorporating a radio-labeled atom (tritium) for further labeling investigations. Both probes were stable in the dark under physiological conditions and could be efficiently photodecomposed at wavelengths above 300 nm, leading to the generation of highly reactive species, aryl cations and cyclohexadienonyl carbene, respectively. In addition, these probes displayed UV-absorption spectra which are compatible with tryptophan-mediated energy transfer photoactivation, which can lead potentially to an efficient mapping of the membrane-associate protein domains.

  DOI：

  10.1021/jo951350k
• 作为产物：
  描述：

  tetradecanoic acid 2,2-dimethyl-1,3-dioxolan-4-ylmethyl ester 以 水 、 溶剂黄146 为溶剂， 反应 4.0h， 以100%的产率得到十四烷酸2,3-二羟丙基酯
  参考文献：
  名称：

  环磷脂酸的合成和水解稳定性：对合成和原始细胞研究的影响

  摘要：

  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。

  DOI：

  10.1039/d2cc00292b

文献信息

• Synthesis of enantiopure ABC-type triacylglycerols
  作者：Haraldur G. Gudmundsson、Kaisa M. Linderborg、Heikki Kallio、Baoru Yang、Gudmundur G. Haraldsson

  DOI：10.1016/j.tet.2019.130813

  日期：2020.1

  the TAGs possess two different saturated fatty acyl groups located in the sn-1 and sn-2 positions with an unsaturated fatty acyl group in the remaining sn-3 position of the glycerol skeleton, whereas the remaining four possess two different saturated acyl groups in the terminal sn-1 and sn-3 positions with an unsaturated acyl group in the sn-2 position. The former group was synthesised by a six-step

  十二种具有三种不同脂肪酸的ABC型对映体纯结构化三酰甘油（TAGs）的合成是通过从（S）-缩酮开始的六步化学酶促方法进行描述的。八个TAG具有位于sn -1和sn -2位置的两个不同的饱和脂肪酰基，在甘油骨架的其余sn -3位置具有不饱和脂肪酰基，而其余​​四个具有两个不同的饱和酰基在终端SN -1和SN -3位置与所述的不饱和酰基SN-2位置。前一组是通过六步化学酶法合成的，涉及高度区域选择性的固定化念珠菌南极脂肪酶。第二组是通过类似的六步法制备的，该方法需要两个独立的脂肪酶步骤。强烈要求此类对映纯TAG作为对油脂中完整TAG进行对映特异性分析的标准。
• LIPOSOMAL COMPOSITIONS
  申请人：Nuvo Research GmbH

  公开号：US20130177629A1

  公开（公告）日：2013-07-11

  The present application includes liposomes and liposomal compositions that comprise chlorite, chlorate or a mixture thereof entrapped inside the liposome core, methods for their preparation and methods of use, in particular as medicaments.

  本申请涉及包括氯酸盐、氯酸盐或两者混合物被包裹在脂质体核内的脂质体和脂质体组成物，它们的制备方法和使用方法，特别是作为药物。
• Specificity of lipoprotein lipase and hepatic lipase toward monoacylglycerols varying in the acyl composition
  作者：Craig H. Miller、J.Wallace Parce、Patricia Sisson、Moseley Waite

  DOI：10.1016/0005-2760(81)90250-2

  日期：1981.9

  report here that both the hepatic lipase and lipoprotein lipase demonstrate specificity towards the acyl group present on monoacylglycerols. We found that unsaturated glycerides are more readily degraded than saturated glycerides. However, the basis for this specificity appears to be different for each enzyme. The activity of the hepatic lipase, but not the lipoprotein lipase, could be stimulated by

  我们在这里报告说，肝脂肪酶和脂蛋白脂肪酶都表现出对单酰基甘油基上存在的酰基的特异性。我们发现不饱和甘油酯比饱和甘油酯更容易降解。但是，每种酶的特异性基础不同。Triton X-100和磷酸甘油酯可以刺激肝脂肪酶的活性，而不是脂蛋白脂肪酶的活性。我们将这些结果解释为表明，尽管脂蛋白脂肪酶和肝脂酶都对底物的物理状态敏感（如荧光去极化所示），但脂蛋白脂肪酶对包含饱和酰基的单酰基甘油的亲和力也很低。
• Synthesis of two new phospholipidic fluorescent probes for membrane studies
  作者：Jean-Philippe Starck、Yoichi Nakatani、Guy Ourisson

  DOI：10.1016/0040-4020(95)00011-v

  日期：1995.2

  Two new fluorenyl-phospholipidic probes have been prepared in good yield by a Pd-0/CuI-catalyzed cross-coupling reaction.
• Biochemical and Molecular Characterization of a Novel Choline-specific Glycerophosphodiester Phosphodiesterase Belonging to the Nucleotide Pyrophosphatase/Phosphodiesterase Family
  作者：Hideki Sakagami、Junken Aoki、Yumiko Natori、Kiyotaka Nishikawa、Yoshiyuki Kakehi、Yasuhiro Natori、Hiroyuki Arai

  DOI：10.1074/jbc.m413438200

  日期：2005.6

  Nucleotide pyrophosphatases/phosphodiesterases (NPPs) are ubiquitous membrane-associated or secreted ectoenzymes that release nucleoside 5'-monophosphate from a variety of nucleotides and nucleotide derivatives. The mammalian NPP family comprises seven members, but only three of these (NPP1-3) have been studied in some detail. Previously we showed that lysophospholipase D, which hydrolyzes lysophosphatidylcholine (LPC) to produce lysophosphatidic acid, is identical to NPP2. More recently an uncharacterized novel NPP member (NPP7) was shown to have alkaline sphingomyelinase activity. These findings raised the possibility that other members of the NPP family act on phospholipids. Here we show that the sixth member of the NPP family, NPP6, is a choline-specific glycerophosphodiester phosphodiesterase. The sequence of NPP6 encodes a transmembrane protein containing an NPP domain with significant homology to NPP4, NPP5, and NPP7/alkaline sphingomyelinase. When expressed in HeLa cells, NPP6 was detected in both the cells and the cell culture medium as judged by Western blotting and by enzymatic activity. Recombinant NPP6 efficiently hydrolyzed the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine, but not the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. In addition, NPP6 hydrolyzed LPC to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. NPP6 showed a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. It also hydrolyzed glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. In mice, NPP6 mRNA was predominantly detected in kidney with a lesser expression in brain and heart, and in human it was detected in kidney and brain. The present results suggest that NPP6 has a specific role through the hydrolysis of polyunsaturated LPC, glycerophosphorylcholine, or sphingosylphosphorylcholine in these organs.