12-((ethoxy(thiocarbonyl))thio)dodecanoic acid | 60908-53-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 12-((ethoxy(thiocarbonyl))thio)dodecanoic acid
• 英文别名: O-Ethyl-S-(11-carboxyundecyl)-dithiocarbonat；12-Ethoxycarbothioylsulfanyldodecanoic acid；12-ethoxycarbothioylsulfanyldodecanoic acid
• CAS: 60908-53-4
• 化学式: C₁₅H₂₈O₃S₂
• 分子量: 320.518
• InChiKey: YBJZHCJTPVNGPF-UHFFFAOYSA-N

物化性质

• 沸点：
  457.2±18.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  12-((ethoxy(thiocarbonyl))thio)dodecanoic acid 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 乙醇 、 二氯甲烷 、 乙二胺 为溶剂， 反应 2.0h， 生成 12-[11-羧基十一烷基硫烷基(苯基)甲基]硫烷基十二烷酸
  参考文献：
  名称：

  Synthesis of a bipolar phosphatidylethanolamine: A model compound for a membrane-spanning probe

  摘要：

  DOI：

  10.1016/s0040-4039(00)96114-8
• 作为产物：
  描述：

  12-溴十二烷酸 、 potassium ethyl xanthogenate 以 丙酮 为溶剂， 反应 24.0h， 以76%的产率得到12-((ethoxy(thiocarbonyl))thio)dodecanoic acid
  参考文献：
  名称：

  A bola-phospholipid bearing tetrafluorophenylazido chromophore as a promising lipid probe for biomembrane photolabeling studies

  摘要：

  为了通过光标记方法研究生物膜，我们合成了一种在跨膜二酰链中间带有四氟苯基叠氮发色团的波拉磷脂探针，并对其进行了表征。该探针显示了波拉脂在巨囊形成过程中的稳定性优势，以及四氟苯叠氮发色团带来的优异光化学特性，因此是一种很有希望用于生物膜光标记研究的探针。

  DOI：

  10.1039/c3ob40659h

文献信息

• Design, synthesis, and properties of a photoactivatable membrane-spanning phospholipidic probe
  作者：Jose M. Delfino、Stuart L. Schreiber、Frederic M. Richards

  DOI：10.1021/ja00062a009

  日期：1993.5

  We introduce here a new photochemical probe suitable for labeling deep into the hydrophobic core of membranes: bis-phosphatidylethanolamine (trifluoromethyl)phenyldiazirine 19 (DIPETPD). This is a bipolar phospholipid provided with a covalently bonded chain designed to span the membrane and equipped with a centrally defined attachment point for the photolabeling group (trifluoromethyl)phenyldiazirine (TPD). This molecule was designed to enhance the geometrical resolution of photochemical labeling of membrane proteins by locating the photoreactive functionality in the center of the bilayer. The remarkable chemical stability of the photoreactive group TPD1 allowed the design of a straightforward and convergent synthetic strategy. The key steps developed for molecules of this new general kind are (a) the mild and efficient coupling of two moieties of N-tBOC-protected lysophosphatidylethanolamine methyl ester to the photoreactive symmetric dicarboxylic fatty acid mediated by dicyclohexylcarbodiimide and (dimethylamino)pyridine and (b) the smooth deprotection of the phosphate and amino functionalities with sodium iodide and trifluoroacetic acid, respectively, to yield the final product. DIPETPD has been successfully incorporated into small and large unilamellar vesicles of different lipid composition and prepared by a variety of procedures. The bilayer location of this reagent (transmembrane vs 'U'-shaped conformations) was assayed by reaction of the amino groups at the polar heads of the bipolar phospholipid with selected membrane-impermeable reagents. Photolysis of the probe incorporated into vesicles occurs readily upon irradiation with UV light (near 360 nm). These 'loaded' vesicles show adequate stability and appear uniform and unilamellar in electron micrographs. They undergo the fusion reaction with influenza virus as efficiently as reagent-free vesicles. Evidence is presented here that DIPETPD and a reductively methylated form efficiently label the peptide ion channel form of gramicidin A (and a chemical analogue) and the influenza virus hemagglutinin. DIPETPD may help to identify transmembrane regions of integral membrane proteins and map the lipid-protein interface in a region known to be deep in the membrane. A new radioactive version of this reagent ([H-3]-DIPETPD)2 has been recently used to ascertain that the HA2 subunit of influenza virus hemagglutinin inserts into the target membrane prior to fusion.3
• A bola-phospholipid bearing tetrafluorophenylazido chromophore as a promising lipid probe for biomembrane photolabeling studies
  作者：Yi Xia、Kheya Sengupta、Alain Maggiani、Fanqi Qu、Ling Peng

  DOI：10.1039/c3ob40659h

  日期：——

  A bola-phospholipid probe, carrying a tetrafluorophenylazido chromophore in the middle of the transmembrane diacyl chain, was synthesized and characterized with a view to studying biomembranes by a photolabeling approach. This probe shows the advantageous stability of bola-lipids in giant vesicle formation alongside excellent photochemical properties conferred by the tetrafluorophenylazido chromophore, and thus constitutes a promising probe for biomembrane photolabeling studies.

  为了通过光标记方法研究生物膜，我们合成了一种在跨膜二酰链中间带有四氟苯基叠氮发色团的波拉磷脂探针，并对其进行了表征。该探针显示了波拉脂在巨囊形成过程中的稳定性优势，以及四氟苯叠氮发色团带来的优异光化学特性，因此是一种很有希望用于生物膜光标记研究的探针。
• Synthesis of a bipolar phosphatidylethanolamine: A model compound for a membrane-spanning probe
  作者：Jose M. Delfino、Charles J. Stankovic、Stuart L. Schreiber、Frederic M. Richards

  DOI：10.1016/s0040-4039(00)96114-8

  日期：——