mono[6-((R)-(-)-2-hydroxymethylpropylamino)-6-deoxy]-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono[6-((R)-(-)-2-hydroxymethylpropylamino)-6-deoxy]-β-cyclodextrin
• 英文别名: mono[6-(R(-)-1-hydroxymethylpropylamino)-6-deoxy]-beta-cyclodextrin；(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5-[[[(2R)-1-hydroxybutan-2-yl]amino]methyl]-10,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• 化学式: C₄₆H₇₉NO₃₅
• 分子量: 1206.12
• InChiKey: QHNMRGORAVHLFN-NWAZHFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.5
• 重原子数：
  82
• 可旋转键数：
  11
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  566
• 氢给体数：
  22
• 氢受体数：
  36

反应信息

• 作为产物：
  描述：

  2-氨基丁醇 、 mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 反应 13.0h， 以71%的产率得到mono[6-((R)-(-)-2-hydroxymethylpropylamino)-6-deoxy]-β-cyclodextrin
  参考文献：
  名称：

  Thermodynamic Origin of Molecular Selective Binding of Bile Salts by Aminated β-Cyclodextrins

  摘要：

  To elucidate quantitatively the sidearm effects on the molecular selective binding of aminated beta-cyclodextrins (beta-CD), microcalorimetry titration has been performed in aqueous phosphate buffer solution (pH = 7.20) at 298.15 K to give the complex stability constants (K-s) and the standard free energy (DeltaGdegrees), enthalpy (DeltaHdegrees), and entropy changes (DeltaSdegrees) for the 1:1 inclusion complexation of beta-CD (1), mono(6-amino-6-deoxy)-beta-CD (2), mono(6-carboxymethylamino-6-deoxy)-beta-CD (3), and mono [6-(R(-)-1-hydroxymethylpropylamino)-6-deoxy]-beta-CD (4) with representative bile salts, deoxycholate, cholate, glycocholate, and taurocholate. The results obtained indicate that the aminated beta-CDs could alter significantly the original molecular binding ability and selectivity of parent beta-CD through the cooperative electrostatic interaction, van der Waals, and hydrophobic interactions between hosts and guests. As compared with parent 1 and aminated beta-CD 2, glycine-modified beta-CD 3 possessing a hydrophilic carboxylic group at the sidearm shows a lower binding ability toward bile salts, attributed to the relatively weaker hydrophobic interactions and the electrostatic repulsion between host and guest to some extent. However, the R(-)-2-amino-1-butanol-modified beta-CD 4 possessing additional binding sites at the chiral sidearm could significantly orient the guest molecules to be included in cavity and thus evidently enhances the molecular binding ability and selectivity through steric interactions. Thermodynamically, the higher complex stability for inclusion complexation of aminated beta-CDs is mainly resulting from enthalpy gain with smaller entropy loss. The combination of calorimetric titration experiments and ROESY spectra establishes the correlation between the thermodynamic parameters and the conformation of the resulting complex, and reveals the factors governing the molecular binding ability and selectivity of bile salts by aminated beta-CDs.

  DOI：

  10.1021/jp036366q

文献信息

• Thermodynamic Origin of Molecular Selective Binding of Bile Salts by Aminated <i>β</i>-Cyclodextrins
  作者：Yu Liu、Ying-Wei Yang、Rui Cao、Shi-Hui Song、Heng-Yi Zhang、Li-Hua Wang

  DOI：10.1021/jp036366q

  日期：2003.12.1

  To elucidate quantitatively the sidearm effects on the molecular selective binding of aminated beta-cyclodextrins (beta-CD), microcalorimetry titration has been performed in aqueous phosphate buffer solution (pH = 7.20) at 298.15 K to give the complex stability constants (K-s) and the standard free energy (DeltaGdegrees), enthalpy (DeltaHdegrees), and entropy changes (DeltaSdegrees) for the 1:1 inclusion complexation of beta-CD (1), mono(6-amino-6-deoxy)-beta-CD (2), mono(6-carboxymethylamino-6-deoxy)-beta-CD (3), and mono [6-(R(-)-1-hydroxymethylpropylamino)-6-deoxy]-beta-CD (4) with representative bile salts, deoxycholate, cholate, glycocholate, and taurocholate. The results obtained indicate that the aminated beta-CDs could alter significantly the original molecular binding ability and selectivity of parent beta-CD through the cooperative electrostatic interaction, van der Waals, and hydrophobic interactions between hosts and guests. As compared with parent 1 and aminated beta-CD 2, glycine-modified beta-CD 3 possessing a hydrophilic carboxylic group at the sidearm shows a lower binding ability toward bile salts, attributed to the relatively weaker hydrophobic interactions and the electrostatic repulsion between host and guest to some extent. However, the R(-)-2-amino-1-butanol-modified beta-CD 4 possessing additional binding sites at the chiral sidearm could significantly orient the guest molecules to be included in cavity and thus evidently enhances the molecular binding ability and selectivity through steric interactions. Thermodynamically, the higher complex stability for inclusion complexation of aminated beta-CDs is mainly resulting from enthalpy gain with smaller entropy loss. The combination of calorimetric titration experiments and ROESY spectra establishes the correlation between the thermodynamic parameters and the conformation of the resulting complex, and reveals the factors governing the molecular binding ability and selectivity of bile salts by aminated beta-CDs.