8-(3-acetylphenyl)-(3',5'-bis-O-(6-azidohexanoyloxy))-2'-deoxyquanosine | 1029857-56-4

• 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: 8-(3-acetylphenyl)-(3',5'-bis-O-(6-azidohexanoyloxy))-2'-deoxyquanosine
• 英文别名: 8-(3-acetylphenyl)-(3',5'-bis-O-(6-azidohexanoyl))-2'-deoxyguanosine；8-(3-acetylphenyl)-3',5'-bis-O-(6-azidohexanoyl)-2'-deoxyguanosine；mAGhaz；[(2R,3S,5R)-5-[8-(3-acetylphenyl)-2-amino-6-oxo-1H-purin-9-yl]-3-(6-azidohexanoyloxy)oxolan-2-yl]methyl 6-azidohexanoate
• CAS: 1029857-56-4
• 化学式: C₃₀H₃₇N₁₁O₇
• 分子量: 663.693
• InChiKey: BUUXUWINRQVNDA-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  48
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  193
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  prop-2-yn-1-yl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate 、 8-(3-acetylphenyl)-(3',5'-bis-O-(6-azidohexanoyloxy))-2'-deoxyquanosine 在 copper(ll) sulfate pentahydrate 、 维生素 C 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到[(2R,3S,5R)-5-[8-(3-acetylphenyl)-2-amino-6-oxo-1H-purin-9-yl]-3-[6-[4-[[3-hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]oxymethyl]triazol-1-yl]hexanoyloxy]oxolan-2-yl]methyl 6-[4-[[3-hydroxy-2-(hydroxymethyl)-2-methylpropanoyl]oxymethyl]triazol-1-yl]hexanoate
  参考文献：
  名称：

  Nonpolymeric Thermosensitive Supramolecules

  摘要：

  Here we show 2'-deoxyguanosine derivatives that self-assemble in aqueous media into discrete supramolecular hexadecamers and exhibit the lower critical solution temperature (LCST) phenomenon. Spectroscopic, calorimetric, and electron microscopy studies support the fact that above the transition temperature (T-t) the supramolecules further assemble into nanoscopic spherical globules of low polydispersity. Furthermore, the T-t can be tuned to higher values by the addition of a more hydrophilic derivative. These findings uncover a new paradigm in the development of smart thermosensitive materials with properties and applications complementary to those of polymers.

  DOI：

  10.1021/ja9070927
• 作为产物：
  描述：

  8-(3-acetylphenyl)-2'-deoxyguanosine 、 6-叠氮基己酸 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到8-(3-acetylphenyl)-(3',5'-bis-O-(6-azidohexanoyloxy))-2'-deoxyquanosine
  参考文献：
  名称：

  Isostructural Self-Assembly of 2′-Deoxyguanosine Derivatives in Aqueous and Organic Media

  摘要：

  We report the self-assembly of a hydrophilic 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) derivative into a discrete and thermally stable hexadecameric supramolecule in aqueous media. We demonstrate that this hexadecamer is isostructural to the one formed by a related lipophilic derivative in organic media. This mAG moiety represents a rare example of a small-molecule recognition motif that is capable of assembling isostructurally and with high fidelity in both organic and aqueous media.

  DOI：

  10.1021/ja8039019

文献信息

• Hexadecameric Self-Assembled Dendrimers Built from 2′-Deoxyguanosine Derivatives
  作者：José E. Betancourt、José M. Rivera

  DOI：10.1021/ol800701j

  日期：2008.6.5

  Herein we describe the construction of hexadecameric self-assembled dendrimers (SADs) using a series of dendronized 8-(m-acetylphenyl)2'-deoxyguanosine (mAG) subunits. The azido-substituted mAG subunits were covalently linked to alkynyl polyester dendrons using a copper-catalyzed 1,3-dipolar cycloaddition reaction. Discrete SADs are formed with high fidelity and thermal stability even with the increased steric hindrance offered by the dendrons.
• Nonpolymeric Thermosensitive Supramolecules
  作者：José E. Betancourt、José M. Rivera

  DOI：10.1021/ja9070927

  日期：2009.11.25

  Here we show 2'-deoxyguanosine derivatives that self-assemble in aqueous media into discrete supramolecular hexadecamers and exhibit the lower critical solution temperature (LCST) phenomenon. Spectroscopic, calorimetric, and electron microscopy studies support the fact that above the transition temperature (T-t) the supramolecules further assemble into nanoscopic spherical globules of low polydispersity. Furthermore, the T-t can be tuned to higher values by the addition of a more hydrophilic derivative. These findings uncover a new paradigm in the development of smart thermosensitive materials with properties and applications complementary to those of polymers.
• Isostructural Self-Assembly of 2′-Deoxyguanosine Derivatives in Aqueous and Organic Media
  作者：Marilyn García-Arriaga、Gerard Hobley、José M. Rivera

  DOI：10.1021/ja8039019

  日期：2008.8.13

  We report the self-assembly of a hydrophilic 8-(m-acetylphenyl)-2'-deoxyguanosine (mAG) derivative into a discrete and thermally stable hexadecameric supramolecule in aqueous media. We demonstrate that this hexadecamer is isostructural to the one formed by a related lipophilic derivative in organic media. This mAG moiety represents a rare example of a small-molecule recognition motif that is capable of assembling isostructurally and with high fidelity in both organic and aqueous media.