methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-7,12-dihydroxy-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 | 873796-84-0

• 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: methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-7,12-dihydroxy-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
• CAS: 873796-84-0
• 化学式: C₄₉H₈₀N₄O₇
• 分子量: 837.197
• InChiKey: ZLSXPUKAVWYEAY-JFSCZXOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  60
• 可旋转键数：
  11
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-7,12-dihydroxy-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 在 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到4-{3-[4-(3-amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoylamino]-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl}-pentanoic acid methyl ester
  参考文献：
  名称：

  Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities

  摘要：

  The hydroxyl at the C-3 of cholic acid was converted to an amino group, and the resulting aminofunctionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in solvent mixtures consisting of mostly nonpolar solvents such as carbon tetrachloride or ethyl acetate/hexane and 2-5% of a polar solvent such as methanol or DMSO. The conformations of the foldamers; were studied by UV, fluorescence, fluorescence quenching, and fluorescence resonance energy transfer. The nature of the polar/nonpolar solvents and their miscibility strongly influenced the folding reaction. Folding was cooperative, as evidenced by the sigmoidal curves in solvent denaturation experiments. The folded conformers became more stable with an increase in the chain length. The folding/unfolding equilibrium was highly sensitive toward the amount of polar solvent. One percent variation in the solvent composition could change the folding free energies by 0.5-1.4 kcal/mol.

  DOI：

  10.1021/ja056151p
• 作为产物：
  描述：

  胆酸甲酯 在 sodium azide 、 偶氮二甲酸二异丙酯 、 水 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 methyl (4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-[[(4R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-azido-7,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-7,12-dihydroxy-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
  参考文献：
  名称：

  Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities

  摘要：

  The hydroxyl at the C-3 of cholic acid was converted to an amino group, and the resulting aminofunctionalized cholic acid was used as a monomer to prepare amide-linked oligomeric cholates. These cholate oligomers fold into helical structures with nanometer-sized hydrophilic internal cavities in solvent mixtures consisting of mostly nonpolar solvents such as carbon tetrachloride or ethyl acetate/hexane and 2-5% of a polar solvent such as methanol or DMSO. The conformations of the foldamers; were studied by UV, fluorescence, fluorescence quenching, and fluorescence resonance energy transfer. The nature of the polar/nonpolar solvents and their miscibility strongly influenced the folding reaction. Folding was cooperative, as evidenced by the sigmoidal curves in solvent denaturation experiments. The folded conformers became more stable with an increase in the chain length. The folding/unfolding equilibrium was highly sensitive toward the amount of polar solvent. One percent variation in the solvent composition could change the folding free energies by 0.5-1.4 kcal/mol.

  DOI：

  10.1021/ja056151p

文献信息

• Cholate−Glutamic Acid Hybrid Foldamer and Its Fluorescent Detection of Zn²⁺
  作者：Zhenqi Zhong、Yan Zhao

  DOI：10.1021/ol071130g

  日期：2007.7.1

  A hybrid foldamer containing six cholate units and two glutamic acids was labeled with two pyrenyl groups at the chain ends. Folding was particularly favorable in the presence of zinc(II), as shown by the enhanced emission of the pyrene excimer. The sensitivity of the detection depended on the relative population of the folded and unfolded conformers, being highest when about 90% of the foldamer was in the unfolded state.