[(3aR,4R,6R,6aR)-4-(2-amino-6-oxo-1H-purin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-(1-adamantylamino)-4-oxobutanoate | 1423523-39-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: [(3aR,4R,6R,6aR)-4-(2-amino-6-oxo-1H-purin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-(1-adamantylamino)-4-oxobutanoate
• CAS: 1423523-39-0
• 化学式: C₂₇H₃₆N₆O₇
• 分子量: 556.619
• InChiKey: DNSWMLIZFYAAHW-CWHZOTDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  168
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  鸟苷 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 高氯酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 [(3aR,4R,6R,6aR)-4-(2-amino-6-oxo-1H-purin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-(1-adamantylamino)-4-oxobutanoate
  参考文献：
  名称：

  From G-quartets to G-ribbon gel by concentration and sonication control

  摘要：

  两种鸟苷类似物通过连接一个（1）或三个金刚烷枝（2）被设计和合成。含有单个金刚烷枝的化合物在乙腈溶液中形成了G四聚体，并在高于临界凝胶化浓度时转变为G丝带凝胶。相较之下，含有三个金刚烷枝的化合物在加热-冷却过程后沉淀。通过圆二色性和紫外/可见光谱、NMR、SEM以及结构研究，充分阐明了G四聚体和G丝带凝胶的形成机制，以及两种化合物自组装模式的差异。化合物1首先在浓度范围5.0 × 10−4到1.0 × 10−2 M的溶液中自组装成G四聚体，随后在浓度进一步增加时，这些G四聚体转变为G丝带。在分子间氢键和疏水相互作用的帮助下，G丝带自组装成六角柱状结构时，发生了凝胶化。该凝胶对超声处理敏感，其形态从柱状结构变化为由薄片组成的花状结构。相对而言，由于空间位阻，化合物2仅基于疏水相互作用组装成球形结构。

  DOI：

  10.1039/c3ob27204d

文献信息

• From G-quartets to G-ribbon gel by concentration and sonication control
  作者：Luyan Meng、Keyin Liu、Shuli Mo、Yueyuan Mao、Tao Yi

  DOI：10.1039/c3ob27204d

  日期：——

  Two guanosine analogues have been designed and synthesized by connecting one (1) or three adamantane branches (2). The compound containing a single adamantane branch formed G-quartets in acetonitrile solution, and was then transformed into a G-ribbon gel at concentrations higher than the critical gelation concentration. In contrast, the compound with three adamantane branches precipitated after a heating–cooling process. By means of circular dichroism and UV/visible spectra, NMR, SEM, and structural studies, the mechanism of the formation of the G-quartets and G-ribbon gel, as well as the difference in the self-assembly modes of the two compounds, have been fully elucidated. Compound 1 firstly self-assembled into G-quartets in solutions in the concentration range 5.0 × 10−4 to 1.0 × 10−2 M, and these G-quartets were transformed into a G-ribbon on further increasing the concentration. Gelation occurred when the G-ribbon self-assembled into a hexagonal columnar structure with the help of intermolecular hydrogen-bonding and hydrophobic interactions. This gel was sensitive to sonication and underwent a morphology change from a columnar structure to a flower-like structure composed of flakes. In contrast, due to steric hindrance, compound 2 only assembled into a spherical structure based on hydrophobic interactions.

  两种鸟苷类似物通过连接一个（1）或三个金刚烷枝（2）被设计和合成。含有单个金刚烷枝的化合物在乙腈溶液中形成了G四聚体，并在高于临界凝胶化浓度时转变为G丝带凝胶。相较之下，含有三个金刚烷枝的化合物在加热-冷却过程后沉淀。通过圆二色性和紫外/可见光谱、NMR、SEM以及结构研究，充分阐明了G四聚体和G丝带凝胶的形成机制，以及两种化合物自组装模式的差异。化合物1首先在浓度范围5.0 × 10−4到1.0 × 10−2 M的溶液中自组装成G四聚体，随后在浓度进一步增加时，这些G四聚体转变为G丝带。在分子间氢键和疏水相互作用的帮助下，G丝带自组装成六角柱状结构时，发生了凝胶化。该凝胶对超声处理敏感，其形态从柱状结构变化为由薄片组成的花状结构。相对而言，由于空间位阻，化合物2仅基于疏水相互作用组装成球形结构。