[(2R)-2-[12-(9H-fluoren-9-ylmethoxycarbonylamino)dodecanoyloxy]-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate | 852385-14-9

• 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: [(2R)-2-[12-(9H-fluoren-9-ylmethoxycarbonylamino)dodecanoyloxy]-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
• CAS: 852385-14-9
• 化学式: C₅₁H₈₃N₂O₁₀P
• 分子量: 915.201
• InChiKey: TWJCNYXUDMDOHX-VZUYHUTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  64
• 可旋转键数：
  41
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R)-2-[12-(9H-fluoren-9-ylmethoxycarbonylamino)dodecanoyloxy]-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 为溶剂， 反应 16.5h， 生成 1-palmitoyl-2-[12'-(PROXYL-3"-carbamoyl)aminolauroyl]-sn-3-glycero-phosphocholine
  参考文献：
  名称：

  A rapid and efficient method for migration-free acylation of lysophospholipids: synthesis of phosphatidylcholines with sn-2-chain-terminal reporter groups

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.02.150
• 作为产物：
  描述：

  棕榈酰氯 在 4-二甲氨基吡啶 、 二正丁基氧化锡 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 73.5h， 生成 [(2R)-2-[12-(9H-fluoren-9-ylmethoxycarbonylamino)dodecanoyloxy]-3-hexadecanoyloxypropyl] 2-(trimethylazaniumyl)ethyl phosphate
  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

• Bio-orthogonal Phosphatidylserine Conjugates for Delivery and Imaging Applications
  作者：Andrew J. Lampkins、Edward J. O’Neil、Bradley D. Smith

  DOI：10.1021/jo8011336

  日期：2008.8.1

  The syntheses of phosphatidylserine (PS) conjugates are described, including fluorescent derivatives for potential cellular delivery and bioimaging applications. Installation of terminal functional groups (amine, thiol, or alkyne) onto the sn-2 chain provides reactive sites for bio-orthogonal conjugation of cargo with suitably protected PS derivatives. An amine-containing PS forms amide bonds with peptidic cargo, a thiol derivative is designed for conjugation to cargo that contain alpha-halo carbonyls or Michael acceptors, and the terminal alkyne PS analogue permits "click" conjugation with any azide-tagged molecule. This latter conjugation method is quite versatile as it can be performed without PS headgroup protection, in aqueous media, and with acid-labile cargo.
• 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 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.
• 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。