β-cyclodextrin * L-phenylalanine | 103928-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-cyclodextrin * L-phenylalanine
• 英文别名: L-phenylalanine*β-cyclodextrin
• CAS: 103928-88-7
• 化学式: C₉H₁₁NO₂*C₄₂H₇₀O₃₅
• 分子量: 1300.19
• InChiKey: JACXPDIPHFMBTL-CYBIHCENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.59
• 重原子数：
  89.0
• 可旋转键数：
  10.0
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  617.37
• 氢给体数：
  23.0
• 氢受体数：
  37.0

反应信息

• 作为产物：
  描述：

  L-苯丙氨酸 、 β-环糊精 以 水 为溶剂， 生成 β-cyclodextrin * L-phenylalanine
  参考文献：
  名称：

  Host–guest inclusion complexes of α and β-cyclodextrins with α-amino acids

  摘要：

  这项创新性研究揭示了所有所列α-氨基酸在α和β-环糊精的疏水腔中形成1:1主客体包合物的形成。根据客体分子的大小和状态研究了包含的热力学参数，以得出对整体结合的贡献的推论。

  DOI：

  10.1039/c4ra07877b

文献信息

• A Thermodynamic Study of the Reactions of Cyclodextrins with Primary and Secondary Aliphatic Alcohols, with D- and L-Phenylalanine, and with L-Phenylalanine Amide
  作者：Mikhail V. Rekharsky、Frederick P. Schwarz、Yadu B. Tewari、Robert N. Goldberg

  DOI：10.1021/j100091a051

  日期：1994.10

  Equilibrium constants and standard molar enthalpies of reaction have been determined by titration calorimetry for the reactions of 1-propanol, 2-propanol, 1-butanol, (R)-(+)-2-butanol, (S)-((-))-2-butanol, (+/-)-butanol, (R)-(+)-2-pentanol, (S)-((-))-2-pentanol, (R)-(+)-2-hexanol, (S)-((-))-2-hexanol, (R)-(+)-2-heptanol, (S)-((-))-2-heptanol, D-phenylalanine, L-phenylalanine, and L-phenylalanineamide with alpha-cyclodextrin and beta-cyclodextrin. The standard molar Gibbs energies, standard molar enthalpies, and standard molar entropies for these reactions correlate well with respect to the number of carbon atoms in the chemical formula of the alcohol and form a series of distinct curves for the different types of alcohols. The results are also discussed in relation to hydrophobic, steric, and charge effects and the exchange reaction for a ligand from alpha-cyclodextrin to beta-cyclodextrin. With the exception of the results for the standard molar enthalpies of reaction of the 2-butanols with alpha-cyclodextrin, the results obtained in this study show that, within the indicated uncertainties, there are no differences in any of the thermodynamic quantities for the reactions of these ligands with either alpha- or beta-cyclodextrin due to the change in the location of a hydrogen atom on an optically active carbon atom.
• Encapsulation of phenylalanine and 3,4-dihydroxyphenylalanine into β-cyclodextrin: Spectral and molecular modeling studies
  作者：A. Antony Muthu Prabhu、G.S. Suresh Kumar、Madi Fatiha、S. Sorimuthu、M. Sundar Raj

  DOI：10.1016/j.molstruc.2014.08.045

  日期：2015.1

  Encapsulation behavior of phenylalanine (PA) and 3,4-dihydroxyphenylalanine (DPA) with beta-cyclodextrin (beta-CD) were analyzed by UV-visible, Fourier transform infrared spectroscopy (FTIR), powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), and molecular modeling methods. The stoichiometric ratio of the inclusion complexes was found to be 1:1 and the binding constant was evaluated using the Benesi-Hildebrand equation. FT-IR, PXRD, and SEM results confirmed the formation of inclusion complexes. PM3 calculations suggest that orientation B is more favored for PA and orientation A is more favored for DPA. The hydrophobic and H-bond interaction between PA/DPA and beta-CD plays an important role in the inclusion complexes. NBO analysis confirmed that mutual interactions formed between occupied and vacant orbitals of both host (beta-CD) and guest (PA/DPA) molecules which is the driving force for the formation of inclusion complexes. (C) 2014 Elsevier B.V. All rights reserved.