(R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid naphthalen-1-ylamide | 873797-03-6

• 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: (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid naphthalen-1-ylamide
• CAS: 873797-03-6
• 化学式: C₃₄H₄₈N₂O₃
• 分子量: 532.767
• InChiKey: XCTFIDXERCZPKI-LXCBOGQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  39.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  95.58
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid naphthalen-1-ylamide 、 在 benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 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 20.0h， 以73%的产率得到
  参考文献：
  名称：

  Environmental Effects Dominate the Folding of Oligocholates in Solution, Surfactant Micelles, and Lipid Membranes

  摘要：

  Oligocholate foldamers with different numbers and locations of guanidinium-carboxylate salt bridges were synthesized. The salt bridges were introduced by incorporating arginine and glutamic acid residues into the foldamer sequence. The conformations of these foldamers were studied by fluorescence spectroscopy in homogeneous solution, anionic and nonionic micelles, and lipid bilayers. Environmental effects instead of inherent foldability were found to dominate the folding. As different noncovalent forces become involved in the conformations of the molecules, the best folder in one environment could turn into the worst in another. Preferential solvation was the main driving force for the folding of oligocholates in solution. The molecules behaved very differently in micelles and lipid bilayers, with the most critical factors controlling the folding-unfolding equilibrium being the solvation of ionic groups and the abilities of the surfactants/lipids to compete for the salt bridge. Because of their ability to fold into helices with a nonpolar exterior and a polar interior, the oligocholates could transport large hydrophilic molecules such as carboxyfluorescein across lipid bilayers. Both the conformational properties of the oligocholates and their binding with the guest were important to the transport efficiency.

  DOI：

  10.1021/ja103694p
• 作为产物：
  描述：

  胆酸甲酯 在 lithium hydroxide 、 sodium azide 、 高氯酸 、 草酰氯 、 偶氮二甲酸二异丙酯 、 水 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 62.5h， 生成 (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid naphthalen-1-ylamide
  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

• 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.