2-油酰基-sn-甘油-3-磷酰胆碱 | 22248-65-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: 2-油酰基-sn-甘油-3-磷酰胆碱
• 英文名称: 2-oleoyl-sn-glycero-3-phosphocholine
• 英文别名: 2-18:1 δ⁹ Lyso PC；[(2R)-3-hydroxy-2-[(Z)-octadec-9-enoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 22248-65-3
• 化学式: C₂₆H₅₂NO₇P
• 分子量: 521.675
• InChiKey: SULIDBRAXVDKBU-PTGWMXDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 海关编码：
  2923900090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2-油酰基-sn-甘油-3-磷酰胆碱 在 Tris buffer 、 4-甲基苯磺酸吡啶 、 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 、 calcium chloride 、 phospholipase A₂ 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 丁酮 为溶剂， 反应 52.0h， 生成
  参考文献：
  名称：

  Synthesis of phosphatidylcholines containing ricinoleic acid

  摘要：

  1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields, The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final products. Several protecting groups were assayed but only beta -methoxyethoxymethyl chloride (MEMCl) and 2,2,2-trichloroethyl chloroformate (TRECCl) gave reasonable yields and good optical purities of the final products. The overall yields for 1,2-diricinoleoyl-sn-glycero-3-phosphocholine and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were 32.1% (with respect to ricinoleic acid methyl ester using TREC as protecting group) and 10.3% (with respect to 1-trityl-glycero-3-phosphochofine), respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01057-2
• 作为产物：
  描述：

  甘磷酸胆碱 在 三氟化硼乙醚 、 sodium 、 zinc(II) chloride 、 O-MEM-ricinoleic acid anhydride 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 2-油酰基-sn-甘油-3-磷酰胆碱
  参考文献：
  名称：

  Synthesis of phosphatidylcholines containing ricinoleic acid

  摘要：

  1,2-Diricinoleoyl- and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were synthesised with good yields, The synthesis started with the preparation of ricinoleic acid from castor oil. The choice of a suitable agent to protect the -OH group of ricinoleic acid was a key factor to afford the final products. Several protecting groups were assayed but only beta -methoxyethoxymethyl chloride (MEMCl) and 2,2,2-trichloroethyl chloroformate (TRECCl) gave reasonable yields and good optical purities of the final products. The overall yields for 1,2-diricinoleoyl-sn-glycero-3-phosphocholine and 1-ricinoleoyl-2-oleoyl-sn-glycero-3-phosphocholine were 32.1% (with respect to ricinoleic acid methyl ester using TREC as protecting group) and 10.3% (with respect to 1-trityl-glycero-3-phosphochofine), respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01057-2

文献信息

• Process for preparing lysophoshatidylcholine
  申请人：CHEMI S.p.A.

  公开号：EP1650215A1

  公开（公告）日：2006-04-26

  What is described is a process for preparing lysophosphatidylcholine by selective monoacylation of glycerophosphorylcholine (I), in the presence of an acylating agent and of dialkyltin derivatives, according to the following diagram: the process being particularly simple and having high overall yields.

  所描述的是通过在酰化剂和二烷基锡衍生物的存在下，通过选择性单酰化甘油磷酸胆碱（I）来制备溶血磷脂酰胆碱的过程，如下图所示： 该过程特别简单且总产率高。
• Lytic reactions of drugs with lipid membranes
  作者：Hannah M. Britt、Clara A. García-Herrero、Paul W. Denny、Jackie A. Mosely、John M. Sanderson

  DOI：10.1039/c8sc04831b

  日期：——

  supplemented with propranolol. This isolation of lipidated drug molecules from liver cells demonstrates a new drug reactivity in living systems. Acyl transfer from lipids to the alcoholic group of propranolol was favoured over transfer to the secondary amine. Migration of acyl groups from the alcohol to the amine was diminished. Other drugs that were examined did not form detectable levels of lipidation products

  普萘洛尔被证明在三种类型的脂膜中发生脂化反应：（1）合成单组分甘油磷脂脂质体；(2)由从大肠杆菌或肝细胞中提取的复杂脂质混合物形成的脂质体；(3) Hep G2 细胞中的纤维素。在补充普萘洛尔的培养基中培养的 Hep G2 细胞的提取物中鉴定出 14 种不同的脂化普萘洛尔同系物。从肝细胞中分离脂质化药物分子证明了生命系统中的新药物反应性。酰基从脂质转移到普萘洛尔的醇基团比转移到仲胺更有利。酰基从醇到胺的迁移减少。所检查的其他药物没有形成可检测水平的脂化产物，但其中许多药物确实影响模型膜中的溶血脂水平。人们发现，化合物在模型系统中诱导溶血脂形成的倾向是纤维素中磷脂沉积活性的预测因子。
• Lipid chain-driven interaction of a lipidated Src-family kinase Lyn with the bilayer membrane
  作者：Shinya Hanashima、Kanako Mito、Yuichi Umegawa、Michio Murata、Hironobu Hojo

  DOI：10.1039/d2ob01079h

  日期：——

  N-Myristoylation is a process of ubiquitous protein modification, which promotes the interaction of lipidated proteins on cell surfaces, in conjunction with reversible S-palmitoylation. We report the cooperative lipid–lipid interaction of two acyl chains of proteins, which increases the protein–membrane interaction and facilitates selective targeting of membranes containing anionic lipids. Lyn is a member

  N-肉豆蔻酰化是一种普遍存在的蛋白质修饰过程，它与可逆的S-棕榈酰化一起促进脂化蛋白质在细胞表面的相互作用。我们报告了两条蛋白质酰基链的协同脂质-脂质相互作用，这增加了蛋白质-膜的相互作用并促进了含有阴离子脂质的膜的选择性靶向。Lyn 是 Src 家族激酶的成员，通过N-肉豆蔻酰和相邻的S分布在膜表面-棕榈酰链锚定在独特的 N 末端结构域。我们制备了脂化 Lyn 的 N 末端短片段，以通过固态核磁共振 (NMR) 分析研究每个酰基链在脂质组成依赖性膜相互作用中的行为。固态31 P-NMR 研究表明，N-肉豆蔻酰化 Lyn 肽的S-棕榈酰化增加了肽和磷脂头基之间的相互作用，特别是与阴离子磷脂酰丝氨酸双分子层的相互作用。具有过氘核N-肉豆蔻酰基链的 Lyn 肽的固态2 H-NMR 表明，在附近存在 N-肉豆蔻酰基链的情况下，N-肉豆蔻酰基链的范围增加（0.6-0.8 Å）。S-棕榈酰链，可能是通过酰基链的相互作用。Lyn
• Synthesis of Lysophosphatidylcholine and Mixed Phosphatidylcholine
  作者：Athanasios Papangelis、Trond Ulven

  DOI：10.1021/acs.joc.2c00335

  日期：2022.6.17

  Lysophosphatidylcholine (LPC) and phosphatidylcholine (PC) are important membrane constituents implicated in signaling and immune regulation. Synthesis of LPCs is challenging due to rapid acyl migration, e.g., induced by chromatography. We here report a highly regioselective synthesis of LPC and mixed PC via an intermediate allowing specific terminal acyl introduction, yielding the pure LPC without

  溶血磷脂酰胆碱 (LPC) 和磷脂酰胆碱 (PC) 是参与信号传导和免疫调节的重要膜成分。由于快速的酰基迁移，例如由色谱法诱导，LPC 的合成具有挑战性。我们在这里报告了 LPC 和混合 PC 的高度区域选择性合成，通过中间体允许特定的末端酰基引入，通过非常温和的 TBS 脱保护产生纯 LPC，无需色谱，使用 1 equiv 的 TFA 在水溶液中。该方法能够合成甘油、酰基和胆碱标记的 LPC。
• Determinants of pH profile and acyl chain selectivity in lysosomal phospholipase A2 [S]
  作者：Vania Hinkovska-Galcheva、Robert Kelly、Kelly A. Manthei、Renee Bouley、Wenmin Yuan、Anna Schwendeman、JohnJ.G. Tesmer、James A. Shayman

  DOI：10.1194/jlr.m084012

  日期：——

  Lysosomal phospholipase A2 (LPLA2) is characterized by broad substrate recognition, peak activity at acidic pH, and the transacylation of lipophilic alcohols, especially N-acetyl-sphingosine. Prior structural analysis of LPLA2 revealed the presence of an atypical acidic residue, Asp13, in the otherwise hydrophobic active site cleft. We hypothesized that Asp13 contributed to the pH profile and/or substrate

  溶酶体磷脂酶A2（LPLA2）的特征是广泛的底物识别，在酸性pH下具有峰值活性以及亲脂性醇（尤其是N-乙酰基-鞘氨醇）的酰基转移。LPLA2的先前结构分析显示，在否则为疏水活性位点的裂口中存在非典型酸性残基Asp13。我们假设Asp13有助于pH谱和/或LPLA2对不饱和酰基链的底物偏爱。为了验证这一假设，我们用Asp13取代了丙氨酸，半胱氨酸或苯丙氨酸。然后，我们监测了1-O-酰基-N-乙酰基鞘氨醇的形成，以测量各种甘油磷脂上sn-1和sn-2酰基的水解情况。在中性pH值下，用Asp13取代产生显着的酶活性（7。4）并干扰了单不饱和和双不饱和酰基链的选择性。但是，该位置在选择酰基受体或甘油磷脂的头基中没有明显作用。我们的模型表明，Asp13及其取代基通过形成易碎的酰基链所占据的疏水轨道的一部分，有助于LPLA2的pH活性曲线和酰基链选择性。