3,7,12-triscarbamyl cholic acid methyl ester

• 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 methyl ester
• 英文别名: methyl (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]pentanoate
• 化学式: C₂₈H₄₅N₃O₈
• 分子量: 551.681
• InChiKey: BFQKPQFVXHECTF-HBCKOZTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  183
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,7,12-triscarbamyl cholic acid methyl ester 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以67%的产率得到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
• 作为产物：
  描述：

  氯磺酰异氰酸酯 、 胆酸甲酯 以 氯仿 为溶剂， 反应 16.0h， 以91%的产率得到3,7,12-triscarbamyl cholic acid methyl ester
  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

文献信息

• Ion Conductors Derived from Cholic Acid and Spermine:  Importance of Facial Hydrophilicity on Na⁺ Transport and Membrane Selectivity
  作者：Prasun Bandyopadhyay、Vaclav Janout、Lan-hui Zhang、Steven L. Regen

  DOI：10.1021/ja010926m

  日期：2001.8.1

  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.