3,7,12-triscarbamyl cholic acid | 361336-22-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3,7,12-triscarbamyl cholic acid
• 英文别名: (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-tricarbamoyloxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 361336-22-3
• 化学式: C₂₇H₄₃N₃O₈
• 分子量: 537.654
• InChiKey: SOMJMNTURBJXKX-MYEOHQFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  194
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  精胺 、 3,7,12-triscarbamyl cholic acid 在 O-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以49%的产率得到N₁,N₂,N₃,N₄-spermine-tetrakis-3,7,12-tricarbamyl-tetracholeamide
  参考文献：
  名称：

  Ion Conductors Derived from Cholic Acid and Spermine:  Importance of Facial Hydrophilicity on Na⁺ Transport and Membrane Selectivity

  摘要：

  A series of ion conductors have been synthesized in which the degree of facial hydrophilicity has been systematically varied. Specifically, conjugates have been prepared from cholic acid and spermine in which the hydrophilic face of each sterol bears methoxy (1), hydroxy (2), carbamate (3), or sulfate groups (4). The ability of these conjugates to promote the transport of Na+ across phosphatidylcholine membranes of varying thickness has been investigated by Na-23 NMR spectroscopy. Examination of observed activities in three different phosphatidylcholine membranes has provided evidence for membrane-spanning dimers as the transport-active species. In the thinnest membranes investigated, made from 1,2-dimyristoleoyl-sn-glycero-3-phosphocholine (C14), Na+-transport activity was found to increase, substantially, with increasing facial hydrophilicity. In thicker membranes, made from 1,2-dioleoyl-sn-glycero-3-phosphocholine (C18), observed activities were found to decrease with increasing facial hydrophilicity; with a membrane of intermediate thickness, prepared from 1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine (C16), ion-conducting activity increased and then decreased, with continuous increases in facial hydrophilicity. The possible origins for these variations in activity are briefly discussed.

  DOI：

  10.1021/ja010926m
• 作为产物：
  描述：

  胆酸甲酯 在 sodium carbonate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 19.0h， 生成 3,7,12-triscarbamyl cholic acid
  参考文献：
  名称：

  Ion Conductors Derived from Cholic Acid and Spermine:  Importance of Facial Hydrophilicity on Na⁺ Transport and Membrane Selectivity

  摘要：

  A series of ion conductors have been synthesized in which the degree of facial hydrophilicity has been systematically varied. Specifically, conjugates have been prepared from cholic acid and spermine in which the hydrophilic face of each sterol bears methoxy (1), hydroxy (2), carbamate (3), or sulfate groups (4). The ability of these conjugates to promote the transport of Na+ across phosphatidylcholine membranes of varying thickness has been investigated by Na-23 NMR spectroscopy. Examination of observed activities in three different phosphatidylcholine membranes has provided evidence for membrane-spanning dimers as the transport-active species. In the thinnest membranes investigated, made from 1,2-dimyristoleoyl-sn-glycero-3-phosphocholine (C14), Na+-transport activity was found to increase, substantially, with increasing facial hydrophilicity. In thicker membranes, made from 1,2-dioleoyl-sn-glycero-3-phosphocholine (C18), observed activities were found to decrease with increasing facial hydrophilicity; with a membrane of intermediate thickness, prepared from 1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine (C16), ion-conducting activity increased and then decreased, with continuous increases in facial hydrophilicity. The possible origins for these variations in activity are briefly discussed.

  DOI：

  10.1021/ja010926m