| 919099-74-4

• 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
• CAS: 919099-74-4
• 化学式: C₉₆H₁₅₆N₆O₁₃
• 分子量: 1602.33
• InChiKey: ZDFVGKRCHHZXGV-PTCOGBJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.27
• 重原子数：
  115.0
• 可旋转键数：
  20.0
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  335.2
• 氢给体数：
  12.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  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 、 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到
  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：

  在 lithium hydroxide 、 水 作用下， 生成
  参考文献：
  名称：

  Efficient Construction of Oligocholate Foldamers via “Click” Chemistry and Their Tolerance of Structural Heterogeneity

  摘要：

  The 1,3-dipolar cycloaddition between an alkynyl-terminated cholate trimer and an azido-functionalized cholate hexamer readily afforded the nonamer and dodecamer derivatives; whereas amide coupling employed in previous oligocholate synthesis failed beyond the octamer. Unlike typical oligocholate foldamers with exclusively head-to-tall arrangement of the repeat units, the newly synthesized "clicked" oligocholates contained head-to-head arrangement and flexible tethers in the sequence. Despite large structural perturbations, the clicked oligocholates folded similarly as the parent foldamers, demonstrating the robustness of the solvophobically driven folding mechanism.

  DOI：

  10.1021/ol802364c

文献信息

• Preferential Solvation within Hydrophilic Nanocavities and Its Effect on the Folding of Cholate Foldamers
  作者：Yan Zhao、Zhenqi Zhong、Eui-Hyun Ryu

  DOI：10.1021/ja0671159

  日期：2007.1.1

  microphase separation of the polar solvent was critical to the folding process. Folding was favored by larger-sized polar solvent molecules, as fewer such molecules could occupy and solvate the nanocavity, thus requiring a smaller extent of phase separation during folding. Folding was also favored by smaller/acyclic nonpolar solvent molecules, probably because they could avoid contact with the OH/NH

  通过荧光和核磁共振光谱研究了三个胆酸盐折叠体和一个分子篮的构象。在与少量极性溶剂（例如，醇或 DMSO）混合的非极性溶剂（例如，己烷/乙酸乙酯或乙酸乙酯）中，胆酸盐低聚物折叠成螺旋状，胆酸盐的亲水面向内翻转。折叠产生亲水性纳米腔，其优先被从本体中浓缩的截留极性溶剂溶剂化。极性溶剂的这种微相分离对折叠过程至关重要。较大尺寸的极性溶剂分子有利于折叠，因为较少的此类分子可以占据和溶剂化纳米腔，因此在折叠过程中需要较小程度的相分离。较小/无环非极性溶剂分子也有利于折叠，
• Enhancing Binding Affinity by the Cooperativity between Host Conformation and Host–Guest Interactions
  作者：Zhenqi Zhong、Xueshu Li、Yan Zhao

  DOI：10.1021/ja203117g

  日期：2011.6.15

  Glutamate-functionalized oligocholate foldamers bound Zn(OAc)(2), guanidine, and even amine compounds with surprisingly high affinities. The conformational change of the hosts during binding was crucial to the enhanced binding affinity. The strongest cooperativity between the conformation and guest-binding occurred when the hosts were unfolded but near the folding-unfolding transition. These results suggest that high binding affinity in molecular recognition may be more easily obtained from large hosts capable of strong cooperative conformational changes instead of those with rigid, preorganized structures.