| 130797-39-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• CAS: 130797-39-6
• 化学式: C₅₄H₈₈NO₈P
• 分子量: 910.268
• InChiKey: WSNBUUDJGQUNRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.49
• 重原子数：
  64.0
• 可旋转键数：
  40.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  111.19
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-(bromomethyl)anthracene 、 1,2-二棕榈酰-外消旋-甘油-3-磷酰[二甲基氨基乙醇] 在 四丁基碘化铵 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以19%的产率得到
  参考文献：
  名称：

  Redox and structural properties of quinone-functionalized phosphatidylcholine liposomes

  摘要：

  Quinone-functionalized liposomes can be prepared by the sonic dispersion of a phosphatidylcholine anthraquinone (DPPC-AQ) with simple phospholipids such as DPPC (at 52-degrees-C) and DOPC (at room temperature). These small (ca. 25-30-nm diameter), unilamellar liposomes typically contain 4-12 mol % phospholipid quinone, which can be reduced and reoxidized by solution reagents. S2O4(2-) rapidly and completely reduces the liposome-bound quinones to the hydroquinone form; Fe(CN)6(3-) rapidly reoxidizes the hydroquinone. BH4- reduces only those quinones situated on the outer surface of the liposome. The rates of redox reactions of the liposome-bound quinones depend on temperature and solution reactant but not on mol % DPPC-AQ in the liposomes or the quinone concentration. The rate law for S2O4(2-) reduction of DPPC-AQ/DOPC, k(obs) = k1k2[S2O4(2-]/(k-1 + k2[S2O4(2-)]), indicates the presence of two kinetically distinct forms of DPPC-AQ. Comparison with the corresponding homogeneous rate constant suggests the identities of the two forms. Manipulation of the transmembrane, distribution of DPPC-AQ (72-98% Q(outer)) is demonstrated by using various phospholipid compositions. Liposomes prepared from the anthracene-functionalized phospholipid DPPC-AN provide a measure of the permeability of the functionalized liposomes. H-1 NMR spectroscopy (500-MHz) reveals the structure and composition of the quinone-functionalized DPPC liposomes. Nuclear Overhauser experiments reveal that the anthraquinone "head group" of DPPC-AQ in DPPC liposomes resides near the hydrophobic-hydrophilic interface and does not extend into solution. Assimilation of these various results leads to a simple, consistent description of these novel biomimetic systems. Applicability of these and related systems as simple, chemical models for respiratory and photosynthetic energy transduction is discussed.

  DOI：

  10.1021/j100157a065