D-Tyr-β-CD | 1242435-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-Tyr-β-CD
• 英文别名: (2R)-3-(4-hydroxyphenyl)-2-[[(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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-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]nonatetracontan-5-yl]methylamino]propanoic acid
• CAS: 1242435-04-6
• 化学式: C₅₁H₇₉NO₃₇
• 分子量: 1298.17
• InChiKey: SFUBYIJHMKOVDZ-ZRXZFYSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -15.8
• 重原子数：
  89
• 可旋转键数：
  12
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  603
• 氢给体数：
  23
• 氢受体数：
  38

反应信息

• 作为产物：
  描述：

  D-酪氨酸 、 mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 在 三乙醇胺 作用下， 以 水 为溶剂， 以41%的产率得到D-Tyr-β-CD
  参考文献：
  名称：

  Thermodynamic Origin of Selective Binding of β-Cyclodextrin Derivatives with Chiral Chromophoric Substituents toward Steroids

  摘要：

  Two beta-cyclodextrin derivatives with chiral chromophoric substituents, that is, L- (1) and D-tyrosine-modified beta-cyclodextrin (2), were synthesized and fully characterized. Their inclusion modes, binding abilities, and molecular selectivities with four steroid guests, that is, cholic acid sodium salt (CA), deoxycholic acid sodium salt (DCA), glycochoic acid sodium salt (GCA), and taurocholic acid sodium salt (TCA), were investigated by the circular dichroism, 2D NMR, and isothermal titration microcalorimetry (ITC). The results obtained from the circular dichroism and 2D NMR showed that two hosts adopted the different binding geometry, and these differences subsequently resulted in the significant differences of molecular binding abilities and selectivities. As compared with native beta-cyclodextrin and tryptophan-modified beta-cyclodextrin, host 2 showed the enhanced binding abilities for CA and DCA but the decreased binding abilities for GCA and TCA, however, host 1 showed the decreased binding abilities for all four bile salts. The best guest selectivity and the best host selectivity were K-S(2-DCA)/K-S(2-TCA) = 12.6 and K-S(2-CA)/K-S(1-CA) = 10, respectively, both exhibiting great enhancement as compared with the corresponding values of the previously reported L- and D-tryptophan-modified beta-cyclodextrins. Thermodynamically, it was the favorable enthalpic gain that led to the high guest selectivity and host selectivity.

  DOI：

  10.1021/jp105821s

文献信息

• Thermodynamic Origin of Selective Binding of β-Cyclodextrin Derivatives with Chiral Chromophoric Substituents toward Steroids
  作者：Yong Chen、Fang Li、Bo-Wen Liu、Bang-Ping Jiang、Heng-Yi Zhang、Li-Hua Wang、Yu Liu

  DOI：10.1021/jp105821s

  日期：2010.12.16

  Two beta-cyclodextrin derivatives with chiral chromophoric substituents, that is, L- (1) and D-tyrosine-modified beta-cyclodextrin (2), were synthesized and fully characterized. Their inclusion modes, binding abilities, and molecular selectivities with four steroid guests, that is, cholic acid sodium salt (CA), deoxycholic acid sodium salt (DCA), glycochoic acid sodium salt (GCA), and taurocholic acid sodium salt (TCA), were investigated by the circular dichroism, 2D NMR, and isothermal titration microcalorimetry (ITC). The results obtained from the circular dichroism and 2D NMR showed that two hosts adopted the different binding geometry, and these differences subsequently resulted in the significant differences of molecular binding abilities and selectivities. As compared with native beta-cyclodextrin and tryptophan-modified beta-cyclodextrin, host 2 showed the enhanced binding abilities for CA and DCA but the decreased binding abilities for GCA and TCA, however, host 1 showed the decreased binding abilities for all four bile salts. The best guest selectivity and the best host selectivity were K-S(2-DCA)/K-S(2-TCA) = 12.6 and K-S(2-CA)/K-S(1-CA) = 10, respectively, both exhibiting great enhancement as compared with the corresponding values of the previously reported L- and D-tryptophan-modified beta-cyclodextrins. Thermodynamically, it was the favorable enthalpic gain that led to the high guest selectivity and host selectivity.