1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine | 17364-17-9

• 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: 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine
• 英文别名: L-α-lysophosphatidylcholine；LPC 16:0；Lysophosphatidylcholine(16:0)；[(2S)-3-hexadecanoyloxy-2-hydroxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 17364-17-9
• 化学式: C₂₄H₅₀NO₇P
• 分子量: 495.637
• InChiKey: ASWBNKHCZGQVJV-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  33
• 可旋转键数：
  24
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine 在 4-二甲氨基吡啶 、 copper(II) sulfate 、 sodium ascorbate 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 水 为溶剂， 反应 35.0h， 生成
  参考文献：
  名称：

  Phosphatidylcholine-Derived Bolaamphiphiles via Click Chemistry

  摘要：

  The copper-catalyzed azide alkyne cycloaddition is employed to modify phosphatidylcholine precursors with sn-2 acyl chains containing terminal alkyne or azide groups. Although the reactions are conducted as biphasic dispersions, the yields are essentially quantitative. Bolaamphiphiles are formed by simply clicking together two phosphatidylcholine alkyne precursors to a central bisazide scaffold. The chemistry introduces polar 1,4-triazole units into the lipophilic region of the bilayer membrane, and the bolaamphiphiles do not form stable vesicles.

  DOI：

  10.1021/ol062557a
• 作为产物：
  描述：

  1.2-Dibenzyl-glycerin-3-palmitinsaeureester 在 钯 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 1-palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Eibl,H.; Westphal,O., Justus Liebigs Annalen der Chemie, 1970, vol. 738, p. 161 - 169

  摘要：

  DOI：

文献信息

• Novel Bioactive Phospholipids:  Practical Total Syntheses of Products from the Oxidation of Arachidonic and Linoleic Esters of 2-Lysophosphatidylcholine¹
  作者：Mingjiang Sun、Yijun Deng、Eugenia Batyreva、Wei Sha、Robert G. Salomon

  DOI：10.1021/jo0105383

  日期：2002.5.1

  Total syntheses of nine novel phospholipids were accomplished to facilitate the identification and biological testing of compounds that are generated upon oxidative cleavage of arachidonate and linoleate esters of 2-lysophosphatidylcholine, the two most abundant polyunsaturated phospholipids in low-density lipoprotein. An efficient general synthesis exploiting 2-lithiofuran as a 4-oxo-2-butenoyl carbanion

  完成了九种新型磷脂的总合成，以简化对低密度脂蛋白中两种最丰富的多不饱和磷脂的2-溶血磷脂酰胆碱的花生四烯酸酯和亚油酸酯的氧化裂解后生成的化合物的鉴定和生物学测试。利用2-硫代呋喃作为4-氧代-2-丁烯酰基碳负离子等效物的有效通用合成提供了含有γ-酮-α，β-不饱和羰基官能团的磷脂。通过利用容易的顺式-反式异构化，可以将两种市售的顺式烯烃（2Z）-2-丁烯-1,4-二醇和2,5-二氢呋喃用作制备霍纳-沃兹沃思-埃蒙斯试剂4的原料。 -（二乙氧基磷酰基）-2E-丁烯醛，是合成2,4-二烯醛的重要组成部分。
• PROCESS
  申请人：DUPONT NUTRITION BIOSCIENCES APS

  公开号：US20160081385A1

  公开（公告）日：2016-03-24

  A method for reducing the amount of cholesterol and/or improving the texture and/or reducing weight loss and/or increasing the fat stability of a meat based food product comprising: a) contacting meat with a lipid acyltransferase; b) incubating the meat contacted with the lipid acyltransferase at a temperature between about 1° C. to about 70° C.; c) producing a food product from the meat; wherein step b) is conducted before, during or after step c). Use of a lipid acyltransferase to reduce cholesterol in a meat based food product.

  一种用于减少胆固醇和/或改善肉类食品产品的质地和/或减少重量损失和/或增加脂肪稳定性的方法，包括：a）将肉类与脂质酰转移酶接触；b）将与脂质酰转移酶接触的肉类在1℃至70℃之间的温度下孵育；c）从肉类制备食品产品；其中步骤b）在步骤c）之前、期间或之后进行。使用脂质酰转移酶来减少肉类食品产品中的胆固醇。
• Controlled Tetradeuteration of Straight‐Chain Fatty Acids: Synthesis, Application, and Insight into the Metabolism of Oxidized Linoleic Acid
  作者：Ayako Watanabe、Kotaro Hama、Kohei Watanabe、Yuko Fujiwara、Kazuaki Yokoyama、Shigeo Murata、Ryo Takita

  DOI：10.1002/anie.202202779

  日期：2022.6.20

  controlled tetradeuteration of straight-chain fatty acids at the α- and β-positions has been developed. The use of four deuterium atoms in fatty acids as well as a diagnostic peak of phosphatidylcholines thus obtained enabled the identification of acyltransferases that transfer the acyl moiety derived from an oxidized linoleic acid, hydroxyoctadecadienoic acid (HODE), to lysophosphatidylcholine.

  已经开发了一种用于在 α 和 β 位置精确控制直链脂肪酸的四氘化的简明方案。使用脂肪酸中的四个氘原子以及由此获得的磷脂酰胆碱的诊断峰能够鉴定将衍生自氧化亚油酸羟基十八碳二烯酸 (HODE) 的酰基部分转移到溶血磷脂酰胆碱的酰基转移酶。
• A clean-up technology for the simultaneous determination of lysophosphatidic acid and sphingosine-1-phosphate by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry using a phosphate-capture molecule, Phos-tag
  作者：Jun-ichi Morishige、Mai Urikura、Haruko Takagi、Kaoru Hirano、Tohru Koike、Tamotsu Tanaka、Kiyoshi Satouchi

  DOI：10.1002/rcm.4484

  日期：2010.4.15

  Phos‐tag complexes at the second partition by adding Phos‐tag. The Phos‐tag complexes of LPA and S1P are detectable by matrix‐assisted laser desorption/ionization time‐of‐flight mass spectrometry (MALDI‐TOFMS) and quantifiable based on the relative intensities of ions using 17:0 LPA and C17 S1P as internal standards. The protocol was validated by analyses of these mediator lipids in calf serum, a rat brain

  溶血磷脂酸（LPA）和鞘氨醇-1-磷酸（S1P）是具有磷酸基的生长因子样脂质。血液中这些介体脂质的浓度被认为是早期发现癌症或血管疾病的潜在生物标记。在这里，我们报告了一种使用Phos-tag（一种锌结合物，与磷酸单酯基团特异性结合）同时测定LPA和S1P的方法。尽管LPA和S1P都是亲水性化合物，但我们发现它们与Phos-tag形成复合物时具有疏水性。基于此发现，我们开发了一种从生物样品中富集LPA和S1P的方法。在由氯仿/甲醇/水（1：1：0.9，v / v / v）组成的两相溶剂系统中进行第一部分分离以去除脂质。通过添加Phos-tag，可以在第二个分区中将LPA和S1P专门提取为Phos-tag复合物。LPA和S1P的Phostag络合物可通过基质辅助激光解吸/电离飞行时间质谱（MALDI-TOFMS）进行检测，并可根据离子的相对强度使用17：0 LPA和C17 S1P作为内部离子进
• Total Synthesis of γ-Hydroxy-α,β-Unsaturated Aldehydic Esters of Cholesterol and 2-Lysophosphatidylcholine
  作者：Yijun Deng、Robert G. Salomon

  DOI：10.1021/jo980861e

  日期：1998.10.1

  Free radical-induced oxidation of polyunsaturated fatty esters in low-density lipoproteins (LDLs) generates 2-lysophosphatidylcholine (PC) and cholesterol esters of gamma-hydroxy-alpha,beta-unsaturated aldehydic acids that covalently modify LDL protein, and protein adducts of the corresponding acids are found in human blood. The chemistry and structures of these compounds resemble those of (E)-4-hydroxy-2-nonenal (HNE), previously considered the most cytotoxic aldehyde released during peroxidation of linoleate and arachidonate esters. The present report details total syntheses of 2-lyse-PC and cholesteryl esters of (E)-9-hydroxy-12-oxododec-10-enoic and (E)-5-hydroxy-8-oxooct-6-enoic acid that presumably are derived in vivo from linoleate and arachidonate esters, respectively. The syntheses depend on the use of a 3,3-dimethyl-2,4-dioxolanyl moiety as a latent aldehyde from which the chemically sensitive gamma-hydroxy-alpha,beta-unsaturated aldehyde array can be generated in the final step. For the cholesteryl esters, generation of the aldehyde group by oxidative cleavage of a vicinal diol could be accomplished in very good yields with periodate. However, for esters of 2-lyso-PC, the target aldehydes were not obtained upon treatment of vicinal diol precursors with periodate owing to a novel oxidative cleavage of the gamma-hydroxy-alpha,beta-unsaturated aldehydes by periodate. Fortunately, treatment of the vicinal diol precursors with Pb(OAc)(4) at -80 degrees C delivered good yields (82-85%) of the desired phospholipid aldehydes.