di-[1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanol-(3'-thio)propionamide] | 817202-05-4

• 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: di-[1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanol-(3'-thio)propionamide]
• CAS: 817202-05-4
• 化学式: C₄₈H₉₄N₂O₁₆P₂S₂
• 分子量: 1081.36
• InChiKey: JTQXHOVULQXLKK-NDOUMJCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.42
• 重原子数：
  70.0
• 可旋转键数：
  53.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  262.78
• 氢给体数：
  6.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  trans-9,10-methyleneoctadecanoic acid 、 di-[1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanol-(3'-thio)propionamide] 在 咪唑 、 N,N'-二环己基碳二亚胺 、 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 6.0h， 以24 mg的产率得到di-[1-palmitoyl-2-trans-9-octadecenoyl-sn-glycero-3-phosphoethanol-(3'-thio)propionamide]
  参考文献：
  名称：

  A Quantitative Assessment of the Influence of Permanent Kinks on the Mixing Behavior of Phospholipids in Cholesterol-Rich Bilayers

  摘要：

  The mixing behavior of a phospholipid containing a cis-cyclopropyl moiety (1) with one that contains two myristoyl groups (3a) has been investigated in fluid bilayers via the nearest-neighbor recognition (NNR) method. In the absence of cholesterol, these lipids mix ideally. In the presence of cholesterol, they show a modest preference for homo-phospholipid association. A trans-form of 1 (i.e., 2) was found to have similar behavior, except that the influence of cholesterol in promoting homo-phospholipid association was greater. Similar results have been found in membranes in which 3a is replaced with a phospholipid bearing two palmitoyol chains (3b). In this case, the effect of the kink is approximately twice as great. The implications of these findings, with respect to the "trans-fatty acid debate", are briefly discussed

  DOI：

  10.1021/ja044517c
• 作为产物：
  描述：

  3,3'-二硫代二丙酸 二(N-羟基丁二酰亚胺酯) 、 1-棕榈-sn-甘油-3-磷酸乙醇胺 在 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 5.0h， 以46%的产率得到di-[1-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanol-(3'-thio)propionamide]
  参考文献：
  名称：

  A Quantitative Assessment of the Influence of Permanent Kinks on the Mixing Behavior of Phospholipids in Cholesterol-Rich Bilayers

  摘要：

  The mixing behavior of a phospholipid containing a cis-cyclopropyl moiety (1) with one that contains two myristoyl groups (3a) has been investigated in fluid bilayers via the nearest-neighbor recognition (NNR) method. In the absence of cholesterol, these lipids mix ideally. In the presence of cholesterol, they show a modest preference for homo-phospholipid association. A trans-form of 1 (i.e., 2) was found to have similar behavior, except that the influence of cholesterol in promoting homo-phospholipid association was greater. Similar results have been found in membranes in which 3a is replaced with a phospholipid bearing two palmitoyol chains (3b). In this case, the effect of the kink is approximately twice as great. The implications of these findings, with respect to the "trans-fatty acid debate", are briefly discussed

  DOI：

  10.1021/ja044517c