(3-月桂酰氧基-2-羟基丙基)2-三甲基铵乙基磷酸酯盐 | 3476-42-4

• 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: (3-月桂酰氧基-2-羟基丙基)2-三甲基铵乙基磷酸酯盐
• 英文名称: 1-O-dodecanoyl-sn-glycero-3-phosphocholine
• 英文别名: 1-mono-lauroylglycerophosphatidylcholine；Lysolpc；(3-dodecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 3476-42-4
• 化学式: C₂₀H₄₂NO₇P
• 分子量: 439.53
• InChiKey: BWKILASWCLJPBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  、 (3-月桂酰氧基-2-羟基丙基)2-三甲基铵乙基磷酸酯盐 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 氯仿 为溶剂， 生成 1-O-dodecanoyl-2-O-[9-[[[2-(tributylstannyl)-4-[(trifluoromethyl)-3H-diazirin-3-yl]benzyl]oxy]carbonyl]nonanoyl]-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  2-(Tributylstannyl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl Alcohol: A Building Block for Photolabeling and Crosslinking Reagents of Very High Specific Radioactivity

  摘要：

  A general approach for the synthesis of novel, radioiodinated photolabeling and cross-linking reagents at no-carrier-added (nea) specific radioactivity (> 2000 Ci/mmol) is described. In this approach, 2-(tributylstannyl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl alcohol 12 serves as a module which, through acylation of its alcohol function, is connected to other structural/functional elements to make the tin-containing precursor forms of the reagents. The final, radioactive compounds are then conveniently prepared in yields varying from 15-50% by electrophilic aromatic substitution of the tributylstannyl group by I-125(+) generated in situ from I-125(-) by peracetic acid. Using this approach, we have synthesized two analogues of phosphatidylcholine (PC) (20 and 21), an analogue of ceramide (36), as well as two heterobifunctional label-transfer cross-linkers (29 and 33). PC 21, examined more closely, is a substrate of the PC-specific phospholipid exchange protein from beef liver and of phospholipase D from cabbage. The latter was utilized to enzymatically convert PC 21 into two additional phospholipids, phosphatidylserine (PS) 25 and phosphatidic acid (PA) 26. Reagents that contain this iodinated photophor also combine desirable photochemical properties. Thus, evidence is presented that they undergo efficient photolysis to generate a (singlet) carbene intermediate which inserts efficiently into hydrocarbon CH bonds. In addition, we demonstrate that the diazirine can be photolyzed in a selective manner, that is, without photodeiodination to occur to a significant extent.

  DOI：

  10.1021/ja00116a013
• 作为产物：
  描述：

  月桂酸乙烯酯 、 2,3-二羟丙基(2-(三甲基铵)乙基)磷酸酯 在 phospholipase A₁ lecitase immobilized on Duolite A₅₆₈ sorbitan monooleic acid ester 作用下， 以 水 为溶剂， 反应 48.0h， 以94.7%的产率得到(3-月桂酰氧基-2-羟基丙基)2-三甲基铵乙基磷酸酯盐
  参考文献：
  名称：

  Process for the production of phospholipids

  摘要：

  一种新的酶法制备1,2-二酰基磷脂的方法，使用一种具有磷脂酶活性的酶制剂，在微水反应体系中对sn-1和sn-2位点进行酰化。更具体地说，根据酯化/转酯化过程生产的1,2-二酰基磷脂可以高产高纯，并在sn-1和sn-2位置携带相同的所需羧酸，优选为脂肪酸，酰基。该过程涉及在上述适当的酶制剂的存在下，将甘油磷脂，优选为甘油磷酸胆碱（GPC），与所需的羧酸，优选为脂肪酸或其衍生物进行酯化/转酯化（酰化）的过程。本发明进一步涉及一种生产1-酰基-2-溶血磷脂，优选为2-溶血磷脂酰基胆碱（2-lyso-PC）的方法，通过在微水介质中，在溶剂的存在下，将甘油磷脂，优选为甘油磷酸胆碱（GPC），与所需的羧酸，优选为脂肪酸或其衍生物，在sn-1特异性磷脂酶（PLA1或PLA1,2）的存在下反应。

  公开号：

  US07034168B2

文献信息

• Phospholipid-Bound Molecular Rotors: Synthesis and Characterization
  作者：Mark A. Haidekker、Thomas Brady、Ke Wen、Cliff Okada、Hazel Y. Stevens、Jeniffer M. Snell、John A. Frangos、Emmanuel A. Theodorakis

  DOI：10.1016/s0968-0896(02)00240-7

  日期：2002.11

  Molecular rotors are fluorescent molecules with a viscosity-sensitive quantum yield that are often used to measure viscosity changes in cell membranes and liposomes. However, commercially available molecular rotors, such as DCVJ (1) do not localize in cell membranes but rapidly migrate into the cytoplasm leading to unreliable measurements of cell membrane viscosity. To overcome this problem, we synthesized

  分子转子是具有粘度敏感量子产率的荧光分子，通常用于测量细胞膜和脂质体中的粘度变化。但是，市售的分子转子，例如DCVJ（1）不在细胞膜中定位，而是迅速迁移到细胞质中，导致细胞膜粘度的测量值不可靠。为了克服这个问题，我们合成了共价连接到磷脂支架的分子转子。将转子基团连接到磷脂酰胆碱（PC）的疏水端不会影响转子的粘度敏感性，并且可以将其充分整合到人工双层膜中，并完全定位在内皮细胞系的质膜中。而且，这些新型转子能够监测磷脂的转变温度。然而，转子基团与磷脂的亲水头的连接导致粘度敏感性的部分损失。磷脂结合的分子转子在细胞质膜中表现出更高的灵敏度和排他性定位，表明这些探针可用于研究膜微粘度。
• 2-(Tributylstannyl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl Alcohol: A Building Block for Photolabeling and Crosslinking Reagents of Very High Specific Radioactivity
  作者：Thomas Weber、Josef Brunner

  DOI：10.1021/ja00116a013

  日期：1995.3

  A general approach for the synthesis of novel, radioiodinated photolabeling and cross-linking reagents at no-carrier-added (nea) specific radioactivity (> 2000 Ci/mmol) is described. In this approach, 2-(tributylstannyl)-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzyl alcohol 12 serves as a module which, through acylation of its alcohol function, is connected to other structural/functional elements to make the tin-containing precursor forms of the reagents. The final, radioactive compounds are then conveniently prepared in yields varying from 15-50% by electrophilic aromatic substitution of the tributylstannyl group by I-125(+) generated in situ from I-125(-) by peracetic acid. Using this approach, we have synthesized two analogues of phosphatidylcholine (PC) (20 and 21), an analogue of ceramide (36), as well as two heterobifunctional label-transfer cross-linkers (29 and 33). PC 21, examined more closely, is a substrate of the PC-specific phospholipid exchange protein from beef liver and of phospholipase D from cabbage. The latter was utilized to enzymatically convert PC 21 into two additional phospholipids, phosphatidylserine (PS) 25 and phosphatidic acid (PA) 26. Reagents that contain this iodinated photophor also combine desirable photochemical properties. Thus, evidence is presented that they undergo efficient photolysis to generate a (singlet) carbene intermediate which inserts efficiently into hydrocarbon CH bonds. In addition, we demonstrate that the diazirine can be photolyzed in a selective manner, that is, without photodeiodination to occur to a significant extent.
• Process for the production of phospholipids
  申请人：Enzymotec Ltd.

  公开号：US07034168B2

  公开（公告）日：2006-04-25

  A new enzymatic process for preparing 1,2-diacylated phospholipids using an enzyme preparation possessing phospholipase activity towards acylation at the sn-1 and sn-2 sites in a microaqueous reaction system. More particularly, the 1,2-diacyl-phospholipids produced according to the esterification/transesterification process are obtainable in high yield and purity and carry identical desired carboxylic acid, preferably fatty acid, acyl groups at the sn-1 and sn-2 positions. The process involves esterification/transesterification (acylation) of a glycerophospholipid, preferably glycerophosphoryl choline (GPC) with a desired carboxylic acid, preferably fatty acid, or their derivatives in the presence of the above mentioned appropriate enzyme preparation. The process of the invention further relates to a process for the production of 1-acyl-2-lyso-glycerophospholipid, preferably 2-lyso-PC by reacting glycerophospholipid, preferably glycerophosphoryl choline (GPC) with a desired carboxylic acid, preferably fatty acid, or their derivatives in the presence of a sn-1 specific phospholipase (PLA1 or PLA1,2) and a solvent, in a microaqueous medium.

  一种新的酶法制备1,2-二酰基磷脂的方法，使用一种具有磷脂酶活性的酶制剂，在微水反应体系中对sn-1和sn-2位点进行酰化。更具体地说，根据酯化/转酯化过程生产的1,2-二酰基磷脂可以高产高纯，并在sn-1和sn-2位置携带相同的所需羧酸，优选为脂肪酸，酰基。该过程涉及在上述适当的酶制剂的存在下，将甘油磷脂，优选为甘油磷酸胆碱（GPC），与所需的羧酸，优选为脂肪酸或其衍生物进行酯化/转酯化（酰化）的过程。本发明进一步涉及一种生产1-酰基-2-溶血磷脂，优选为2-溶血磷脂酰基胆碱（2-lyso-PC）的方法，通过在微水介质中，在溶剂的存在下，将甘油磷脂，优选为甘油磷酸胆碱（GPC），与所需的羧酸，优选为脂肪酸或其衍生物，在sn-1特异性磷脂酶（PLA1或PLA1,2）的存在下反应。