methyl N-dansyl-3α-amino-7α,12α-dihydroxy-5β-cholan-24-oate | 873796-95-3

• 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 N-dansyl-3α-amino-7α,12α-dihydroxy-5β-cholan-24-oate
• CAS: 873796-95-3
• 化学式: C₃₇H₅₄N₂O₆S
• 分子量: 654.912
• InChiKey: OBLFCPHRFWVBOE-FBGMXJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.74
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  116.17
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl N-dansyl-3α-amino-7α,12α-dihydroxy-5β-cholan-24-oate 在 甲醇 、 potassium hydroxide 作用下， 生成 N-dansyl-3β-amino-7α,12α-dihydroxy-5β-cholan-24-oic acid
  参考文献：
  名称：

  Two-channel dansyl/tryptophan emitters with a cholic acid bridge as reporters for local hydrophobicity within supramolecular systems based on bile salts

  摘要：

  在仿生介质中，由于碘离子的存在，与Trp和Dns荧光团结合的偶联双聚体同时发射的发射被抑制，其速率常数取决于局部疏水性。

  DOI：

  10.1039/c4ob01394h
• 作为产物：
  描述：

  胆酸甲酯 在 吡啶 、 sodium azide 、 palladium 10% on activated carbon 、 甲酸铵 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl N-dansyl-3α-amino-7α,12α-dihydroxy-5β-cholan-24-oate
  参考文献：
  名称：

  Two-channel dansyl/tryptophan emitters with a cholic acid bridge as reporters for local hydrophobicity within supramolecular systems based on bile salts

  摘要：

  在仿生介质中，由于碘离子的存在，与Trp和Dns荧光团结合的偶联双聚体同时发射的发射被抑制，其速率常数取决于局部疏水性。

  DOI：

  10.1039/c4ob01394h

文献信息

• Synthesis of new, UV-photoactive dansyl derivatives for flow cytometric studies on bile acid uptake
  作者：Jana Rohacova、M. Luisa Marin、Alicia Martínez-Romero、José-Enrique O'Connor、M. Jose Gomez-Lechon、M. Teresa Donato、Jose V. Castell、Miguel A. Miranda

  DOI：10.1039/b912134j

  日期：——

  Four new fluorescent derivatives of cholic acid have been synthesized; they incorporate a dansyl moiety at 3α-, 3β-, 7α- or 7β- positions. These cholic acid analogs are UV photoactive and also exhibit green fluorescence. In addition, they have been demonstrated to be suitable for studying the kinetics of bile acid transport by flow cytometry.

  已合成四种新的氟荧光胆酸衍生物；它们在3α-、3β-、7α-或7β-位点上引入了丹酰基团。这些胆酸类类似物具有紫外光光活性，并且表现出绿色荧光。此外，已证明它们适合通过流式细胞术研究胆酸运输的动力学。
• Oligomeric Cholates:  Amphiphilic Foldamers with Nanometer-Sized Hydrophilic Cavities
  作者：Yan Zhao、Zhenqi Zhong

  DOI：10.1021/ja056151p

  日期：2005.12.1

  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.