L-Trp-β-CD | 221216-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-Trp-β-CD
• 英文别名: L-Trp-beta-Cyclodextrin；(2S)-3-(1H-indol-3-yl)-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: 221216-87-1
• 化学式: C₅₃H₈₀N₂O₃₆
• 分子量: 1321.21
• InChiKey: IIWMNPUYSSMIEG-UEYSVTHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -15.3
• 重原子数：
  91
• 可旋转键数：
  12
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  599
• 氢给体数：
  23
• 氢受体数：
  37

反应信息

• 作为反应物：
  描述：

  冰片 、 L-Trp-β-CD 在 phosphate buffer 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Molecular Recognition Study on Supramolecular Systems. 20. Molecular Recognition and Enantioselectivity of Aliphatic Alcohols by l-Tryptophan-Modified β-Cyclodextrin

  摘要：

  L-Tryptophan-modified beta-cyclodextrin (L-Trp-beta-CD) has been synthesized and its molecular recognition behavior investigated through fluorescence and circular dichroism spectrometry, as well as fluorescence lifetime measurement in the presence and absence of various alcohols as guest molecules. Employing the indolyl group as a spectral probe, spectrofluorometric and spectropolarimetric titrations have been performed in aqueous phosphate buffer solution at pH 7.20 to calculate the complex stability constants for 1:1 inclusion complexation of L-Trp-beta-CD with several series of alcohols at 25 degrees C. The results obtained indicate that L-Trp-beta-CD can recognize not only size/shape and hydrophobicity but also the enantiomeric and geometrical isomers of the guest alcohols, showing a 230-fold molecular selectivity (13.5 kJ mol(-1)) for 2-adamantanol over cyclopentanol among the cyclic alcohols examined. Moderate enantiomeric selectivities of 1.2 and 1.9 for (-)-isomers of borneol and menthol, respectively, and geometrical selectivity of 2.0 for geraniol over nerol have also been observed.

  DOI：

  10.1021/jo981891k
• 作为产物：
  描述：

  L-色氨酸 、 mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 在 三乙醇胺 作用下， 以 水 为溶剂， 以16%的产率得到L-Trp-β-CD
  参考文献：
  名称：

  β-环糊精与氨基酸偶联的量子点纳米粒子靶向细胞摄取和siRNA沉默

  摘要：

  量子点（QD）有可能用作光稳定的信标来跟踪siRNA的传递，这正迅速成为一种探寻细胞中基因功能的诱人方法。在本文中，我们通过直接的配体交换反应合成了包覆有β-环糊精（β-CD）的QD纳米粒子，该纳米粒子与具有不同表面电荷（正，负和中性）的氨基酸偶联，并用于传递siRNA。我们发现，这些量子点是在分流生物缓冲器具有高胶体稳定性，并具有相似的三-强的光发射性质Ñ -octylphosphine氧化膦（TOPO）包被的量子点，并且还具有长荧光寿命（12.5ns的用于大号-His-β-CD涂层的CdSe / ZnSe量子点）。这些修饰的QD在正常细胞和癌细胞中的体外细胞毒性和内在化结果表明，与氨基酸外层偶联的β-CD大大提高了QD的生物相容性，即使在非常高的浓度下也具有较低的细胞毒性。尤其是，涂有L -His-β-CD的CdSe / ZnSe QD对这些细胞的细胞毒性较低（CC 50值为180.6±3

  DOI：

  10.1002/chem.201003523

文献信息

• Giant Nanotubes Loaded with Artificial Peroxidase Centers: Self-Assembly of Supramolecular Amphiphiles as a Tool To Functionalize Nanotubes
  作者：Yong Tang、Lipeng Zhou、Jiaxi Li、Quan Luo、Xin Huang、Ping Wu、Yongguo Wang、Jiayun Xu、Jiacong Shen、Junqiu Liu

  DOI：10.1002/anie.200907036

  日期：2010.5.25

  Test tubes: Large‐diameter nanotubes have been obtained by direct self‐assembly of cyclodextrin‐based host–guest superamphiphiles (see picture). By manipulating the surface of the nanotubes with a combination of a molecular‐imprinting strategy and self‐assembly, the main catalytic components of glutathione peroxidase were fabricated on the nanotube scaffold.

  试管：大直径的纳米管是通过基于环糊精的宿主-客体超两亲物的直接自组装获得的（见图）。通过结合分子印迹策略和自组装操作纳米管的表面，在纳米管支架上制备了谷胱甘肽过氧化物酶的主要催化成分。
• Supramolecular Aggregates Constructed from Gold Nanoparticles and <scp>l</scp>-Try-CD Polypseudorotaxanes as Captors for Fullerenes
  作者：Yu Liu、Hao Wang、Yong Chen、Chen-Feng Ke、Min Liu

  DOI：10.1021/ja046294w

  日期：2005.1.1

  A series of cycloclextrin-based polypseudorotaxanes (PPRs) were constructed by threading native beta-cyclodextrin or L-tryptophan-modified beta-cyclodextrin onto the amino-terminated PPG chains of different lengths. Subsequently, these PPRs were further assembled to form netlike supramolecular aggregates through the linkage of gold nanoparticles, and the resulting water-soluble Au-PPR aggregates were comprehensively characterized by FT-IR, UV, NMR, fluorescence spectroscopy, powder X-ray diffraction patterning, TG-DTA, and transmission electron microscopy. The results showed that the size and sedimentation rate of the Au-PPR aggregates were mainly dependent on the lengths of the PPG Chains. Significantly, the Au-PPR aggregate 8, involving many L-tryptophan residues, showed not only a satisfactory water solubility but also a good capturing ability for fullerenes in aqueous solution. The 8-fullerene conjugate thus formed exhibited a good DNA cleavage ability under light irradiation.