1-palmitoyl-2-(12'-aminolauroyl)-sn-glycero-3-phosphocholine | 250142-34-8

• 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-(12'-aminolauroyl)-sn-glycero-3-phosphocholine
• 英文别名: [(2R)-2-(12-aminododecanoyloxy)-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 250142-34-8
• 化学式: C₃₆H₇₃N₂O₈P
• 分子量: 692.958
• InChiKey: KRAHDIXVPJCBCA-UUWRZZSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  47
• 可旋转键数：
  37
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-palmitoyl-2-(12'-aminolauroyl)-sn-glycero-3-phosphocholine 在 4-叔丁基异氰酸苯酯 作用下， 以 氯仿 为溶剂， 以66 mg的产率得到
  参考文献：
  名称：

  Membrane Transporters for Anions That Use a Relay Mechanism

  摘要：

  A new type of synthetic membrane transporter is described and shown to operate in vesicles by a relay mechanism. The transporter structure is a phosphatidylcholine derivative with a urea group appended to the end of its sn-2 acyl chain. The urea can bind a chloride ion at the membrane surface via hydrogen bonds and then relay it through the bilayer interior to an acceptor molecule located in the opposite membrane leaflet. Three phosphatidylcholine derivatives were studied and transport rates increased with transporter affinity for chloride. The results of various controls studies are consistent with an anion countertransport process using a relay mechanism and a kinetically active aggregate of two or four transporter molecules. Transport is inhibited if the transporter resides in only one leaflet of the membrane, if the bilayer is too thick, and if the counteranion is sulfate dianion. The expected favorable formulation properties of these amphiphilic compounds should facilitate efforts to transform them into tools for biomedical research and perhaps as therapeutic agents.

  DOI：

  10.1021/ja8082363
• 作为产物：
  描述：

  Fmoc-12-氨基十二烷酸 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 72.0h， 生成 1-palmitoyl-2-(12'-aminolauroyl)-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  光响应跨膜阴离子转运继电器

  摘要：

  生物学中跨脂质膜的离子传输由刺激响应膜通道和分子机器离子泵（例如 ATP 酶）控制。在这里，我们报告了一种合成的类似分子机器的离子传输中继器，其中脂质双层膜相对两侧的转运蛋白通过在它们之间传递离子来促进传输。通过将光响应伸缩臂纳入继电器设计中，该过程可响应蓝光和绿光照射而得到可逆控制。当臂的长度足以使阴离子在位于膜相对两侧的转运蛋白之间通过时，转运仅发生在延伸状态下。相反，伸缩臂的收缩状态太短，无法实现有效的运输。该系统充当类似机器组件的刺激响应整体，让人想起工厂装配线上的机械臂，协同工作以调节离子传输。这项工作指出了使用脂质双层膜作为限制、定向和控制分子机器相对位置的支架的新前景，从而使多个组件能够协同工作，并在生物领域开辟新的应用。

  DOI：

  10.1021/jacs.2c02612

文献信息

• A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of <scp>l</scp>-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives
  作者：Farzaneh S. Roodsari、Dongpei Wu、Gregory S. Pum、Joseph Hajdu

  DOI：10.1021/jo990414e

  日期：1999.10.1

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.
• A rapid and efficient method for migration-free acylation of lysophospholipids: synthesis of phosphatidylcholines with sn-2-chain-terminal reporter groups
  作者：Renato Rosseto、Joseph Hajdu

  DOI：10.1016/j.tetlet.2005.02.150

  日期：2005.4

  A rapid and efficient method for migration-free acylation of lysophosphatidylcholines has been developed using ultrasound for agitation of the reaction mixture and glass beads for increasing the surface in the reaction vessel. The products were obtained in good yields and short reaction times. The method has been applied for the preparation of a variety of substituted phospholipid substrates. (c) 2005 Published by Elsevier Ltd.
• Membrane Transporters for Anions That Use a Relay Mechanism
  作者：Beth A. McNally、Edward J. O’Neil、Anh Nguyen、Bradley D. Smith

  DOI：10.1021/ja8082363

  日期：2008.12.24

  A new type of synthetic membrane transporter is described and shown to operate in vesicles by a relay mechanism. The transporter structure is a phosphatidylcholine derivative with a urea group appended to the end of its sn-2 acyl chain. The urea can bind a chloride ion at the membrane surface via hydrogen bonds and then relay it through the bilayer interior to an acceptor molecule located in the opposite membrane leaflet. Three phosphatidylcholine derivatives were studied and transport rates increased with transporter affinity for chloride. The results of various controls studies are consistent with an anion countertransport process using a relay mechanism and a kinetically active aggregate of two or four transporter molecules. Transport is inhibited if the transporter resides in only one leaflet of the membrane, if the bilayer is too thick, and if the counteranion is sulfate dianion. The expected favorable formulation properties of these amphiphilic compounds should facilitate efforts to transform them into tools for biomedical research and perhaps as therapeutic agents.
• A Photo-responsive Transmembrane Anion Transporter Relay
  作者：Toby G. Johnson、Amir Sadeghi-Kelishadi、Matthew J. Langton

  DOI：10.1021/jacs.2c02612

  日期：2022.6.15

  relay, in which transporters on opposite sides of a lipid bilayer membrane facilitate transport by passing ions between them. By incorporating a photo-responsive telescopic arm into the relay design, this process is reversibly controlled in response to irradiation with blue and green light. Transport occurs only in the extended state when the length of the arm is sufficient to pass the anion between transporters

  生物学中跨脂质膜的离子传输由刺激响应膜通道和分子机器离子泵（例如 ATP 酶）控制。在这里，我们报告了一种合成的类似分子机器的离子传输中继器，其中脂质双层膜相对两侧的转运蛋白通过在它们之间传递离子来促进传输。通过将光响应伸缩臂纳入继电器设计中，该过程可响应蓝光和绿光照射而得到可逆控制。当臂的长度足以使阴离子在位于膜相对两侧的转运蛋白之间通过时，转运仅发生在延伸状态下。相反，伸缩臂的收缩状态太短，无法实现有效的运输。该系统充当类似机器组件的刺激响应整体，让人想起工厂装配线上的机械臂，协同工作以调节离子传输。这项工作指出了使用脂质双层膜作为限制、定向和控制分子机器相对位置的支架的新前景，从而使多个组件能够协同工作，并在生物领域开辟新的应用。