8-(3-acetylphenyl)-2'-deoxyguanosine

• 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)-2'-deoxyguanosine
• 英文别名: 8-(m-acetylphenyl)-20-deoxyguanosine；8-(m-acetylphenyl)-2'-deoxyguanosine；mAG；8-(3-acetylphenyl)-2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• 化学式: C₁₈H₁₉N₅O₅
• 分子量: 385.379
• InChiKey: MPPJYLUOGREELN-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(3-acetylphenyl)-2'-deoxyguanosine 在 4-二甲氨基吡啶 、 三乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 生成 8-(4-methoxychalcone)-(3',5'-bis-O-isobutyryl)-2'-deoxyguanosine
  参考文献：
  名称：

  A Photoresponsive Supramolecular G-Quadruplex

  摘要：

  Photoirradiation of a hexadecameric supramolecular G-quadruplex leads to a diastereoselective [2 + 2] cyclodimerization of half of its constituent subunits, which in turn shifts the equilibrium toward the formation of a precise heteromeric octamer.

  DOI：

  10.1021/ol400610x
• 作为产物：
  描述：

  2'-脱氧鸟苷 在 N-溴代丁二酰亚胺(NBS) 、 palladium diacetate 作用下， 以 水 、 乙腈 为溶剂， 生成 8-(3-acetylphenyl)-2'-deoxyguanosine
  参考文献：
  名称：

  通过自组装增强发射来 跟踪超分子G四链体的形成†

  摘要：

  我们报告了两个亲脂性的2'-脱氧鸟苷（G）衍生物的合成和自组装，其荧光强度通过自组装成超分子G-四链体（SGQs）进行调节。两种衍生物均以同构结构自组装，其中一种显示最高100％的发射增强，而另一种显示初始增强，然后淬灭10％。因此，自组装产生的旋转限制足以引起发射的显着变化，但是考虑荧光团之间的特定相互作用至关重要，因为它们将决定最终的发射特征。这些发现可能为发光超分子传感器和探针的发展打开大门。

  DOI：

  10.1039/c6ob02586b

文献信息

• Supramolecular hacky sacks (SHS), method of synthesis and applications thereof
  申请人：Rivera Jose M

  公开号：US10106572B1

  公开（公告）日：2018-10-23

  The invention is directed to small molecules that self-assemble hierarchically to form NPs termed SHS (due to their architectural features). These SHS are composed by precise supramolecules known as Supramolecular G-Quadruplexes (SGQs) which are formed when amphiphilic guanosine (G) derivatives that self-assemble in presence of salt by non-covalent interactions. The resulting SGQs are made of amphiphilic guanosine (G) subunits (with precisely eight subunits at neutral pH (pH>5.7) or sixteen subunits at acidic pH (pH<5.7)). The SGQs are responsive entities that further self-assemble upon an external stimulus, such as an increase in temperature or a change in pH, leading to the formation of the aforementioned SHS.

  本发明涉及小分子自组装成分层结构形成的纳米粒子，称为SHS（由于其结构特征而得名）。这些SHS由精确的超分子组成，称为超分子G四链体（SGQs），当两性鸟嘌呤（G）衍生物在盐存在下通过非共价作用自组装时形成。所得到的SGQs由两性鸟嘌呤（G）亚基组成（在中性pH（pH>5.7）下精确地有八个亚基，在酸性pH（pH<5.7）下有十六个亚基）。SGQs是响应性实体，可进一步自组装以响应外部刺激，例如温度升高或pH值变化，从而形成上述的SHS。
• 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.
• Expanding the Hoogsteen Edge of 2‘-Deoxyguanosine:  Consequences for G-Quadruplex Formation
  作者：Vladimir Gubala、José E. Betancourt、José M. Rivera

  DOI：10.1021/ol048013v

  日期：2004.12.1

  The synthesis and self-assembling properties of 8-aryl-2'-deoxyguanosine derivatives are described. Our studies suggest that a properly placed acetyl group can increase the stability and specificity of the resulting G-quadruplex supramolecules by enhancing noncovalent interactions such as hydrogen bonds and z-stacking.
• 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.