[(2R)-3-[2-[3-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]propanoylamino]ethoxy-hydroxyphosphoryl]oxy-2-tetradecanoyloxypropyl] tetradecanoate | 628339-29-7

• 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: [(2R)-3-[2-[3-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]propanoylamino]ethoxy-hydroxyphosphoryl]oxy-2-tetradecanoyloxypropyl] tetradecanoate
• CAS: 628339-29-7
• 化学式: C₆₆H₁₁₉N₂O₁₁PS₂
• 分子量: 1211.78
• InChiKey: MPSQXHMFHLDQFJ-PPVGSBBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20
• 重原子数：
  82
• 可旋转键数：
  50
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  226
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2R)-3-[2-[3-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]propanoylamino]ethoxy-hydroxyphosphoryl]oxy-2-tetradecanoyloxypropyl] tetradecanoate 在 sodium hydroxide 、 1,4-二巯基-2,3-丁二醇 作用下， 生成 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate 、 Tetradecanoic acid (R)-2-({2-[3-(2-{2-[((R)-2,3-bis-tetradecanoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethylcarbamoyl}-ethyldisulfanyl)-propionylamino]-ethoxy}-hydroxy-phosphoryloxy)-1-tetradecanoyloxymethyl-ethyl ester
  参考文献：
  名称：

  Selective Sterol-Phospholipid Associations in Fluid Bilayers

  摘要：

  The nearest-neighbor preferences of three exchangeable lipid monomers (two phospholipids that differ in length, A and B, and a derivative of cholesterol, C) have been quantified in the fluid bilayer state by use of the nearest-neighbor recognition method (Davidson, S. K. M.; Regen, S. L. Chem. Rev. 1997, 97, 1269). Thus, an analysis of the equilibrium dimer distributions has shown that (i) the sterol favors both phospholipids as nearest neighbors relative to other sterol molecules, (ii) that this recognition is selective (i,e., the sterol favors the longer phospholipid as a nearest neighbor over the shorter one, especially when the sterol concentrations in the bilayer is high (e.g., 40 mol %), and (iii) the phospholipids, themselves, are unable to recognize each other. Taken together, these findings indicate that the probable mechanism by which cholesterol induces homoassociation of A and B in analogous bilayers is one in which the sterol "pulls" two or more of the longer phospholipid monomers (B) out of a "sea" of randomly mixed A and B. These findings also lend support for the notion of cholesterol - phospholipid complexation in fluid bilayers. The biological implications of these findings are briefly discussed.

  DOI：

  10.1021/ja017269i
• 作为产物：
  描述：

  [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] N-[2-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]ethyl]carbamate 、 Tetradecanoic acid (R)-2-({2-[3-(2-{2-[((R)-2,3-bis-tetradecanoyloxy-propoxy)-hydroxy-phosphoryloxy]-ethylcarbamoyl}-ethyldisulfanyl)-propionylamino]-ethoxy}-hydroxy-phosphoryloxy)-1-tetradecanoyloxymethyl-ethyl ester 在 sodium hydroxide 、 1,4-二巯基-2,3-丁二醇 作用下， 生成 [(2R)-3-[2-[3-[2-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]ethyldisulfanyl]propanoylamino]ethoxy-hydroxyphosphoryl]oxy-2-tetradecanoyloxypropyl] tetradecanoate
  参考文献：
  名称：

  Selective Sterol-Phospholipid Associations in Fluid Bilayers

  摘要：

  The nearest-neighbor preferences of three exchangeable lipid monomers (two phospholipids that differ in length, A and B, and a derivative of cholesterol, C) have been quantified in the fluid bilayer state by use of the nearest-neighbor recognition method (Davidson, S. K. M.; Regen, S. L. Chem. Rev. 1997, 97, 1269). Thus, an analysis of the equilibrium dimer distributions has shown that (i) the sterol favors both phospholipids as nearest neighbors relative to other sterol molecules, (ii) that this recognition is selective (i,e., the sterol favors the longer phospholipid as a nearest neighbor over the shorter one, especially when the sterol concentrations in the bilayer is high (e.g., 40 mol %), and (iii) the phospholipids, themselves, are unable to recognize each other. Taken together, these findings indicate that the probable mechanism by which cholesterol induces homoassociation of A and B in analogous bilayers is one in which the sterol "pulls" two or more of the longer phospholipid monomers (B) out of a "sea" of randomly mixed A and B. These findings also lend support for the notion of cholesterol - phospholipid complexation in fluid bilayers. The biological implications of these findings are briefly discussed.

  DOI：

  10.1021/ja017269i

文献信息

• The Structural Role of Cholesterol in Biological Membranes
  作者：Michihiro Sugahara、Maki Uragami、Xun Yan、Steven L. Regen

  DOI：10.1021/ja016199c

  日期：2001.8.1
• Selective Sterol-Phospholipid Associations in Fluid Bilayers
  作者：Michihiro Sugahara、Maki Uragami、Steven L. Regen

  DOI：10.1021/ja017269i

  日期：2002.4.1

  The nearest-neighbor preferences of three exchangeable lipid monomers (two phospholipids that differ in length, A and B, and a derivative of cholesterol, C) have been quantified in the fluid bilayer state by use of the nearest-neighbor recognition method (Davidson, S. K. M.; Regen, S. L. Chem. Rev. 1997, 97, 1269). Thus, an analysis of the equilibrium dimer distributions has shown that (i) the sterol favors both phospholipids as nearest neighbors relative to other sterol molecules, (ii) that this recognition is selective (i,e., the sterol favors the longer phospholipid as a nearest neighbor over the shorter one, especially when the sterol concentrations in the bilayer is high (e.g., 40 mol %), and (iii) the phospholipids, themselves, are unable to recognize each other. Taken together, these findings indicate that the probable mechanism by which cholesterol induces homoassociation of A and B in analogous bilayers is one in which the sterol "pulls" two or more of the longer phospholipid monomers (B) out of a "sea" of randomly mixed A and B. These findings also lend support for the notion of cholesterol - phospholipid complexation in fluid bilayers. The biological implications of these findings are briefly discussed.