8-(octadec-1-yn-1-yl)adenosine | 791114-20-0

• 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: 8-(octadec-1-yn-1-yl)adenosine
• 英文别名: 8-Octadec-1-yn-1-yladenosine；(2R,3R,4S,5R)-2-(6-amino-8-octadec-1-ynylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 791114-20-0
• 化学式: C₂₈H₄₅N₅O₄
• 分子量: 515.696
• InChiKey: PPRDWWDPYMJSDR-VGSCBBJJSA-N

物化性质

• 熔点：
  134-138 °C(Solv: ethanol (64-17-5); ethyl ether (60-29-7))
• 沸点：
  734.2±70.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-(octadec-1-yn-1-yl)adenosine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 80.0 ℃ 、10.13 MPa 条件下， 反应 24.0h， 以97%的产率得到8-octadodecyladenosine
  参考文献：
  名称：

  Lipophilic Nucleosides by Sonogashira Coupling

  摘要：

  通过 5-碘尿苷、8-溴腺苷和受保护的 8-溴鸟苷或相关卤代核酸的 Sonogashira 偶联，可以直接获得 N-杂环上带有亲脂性炔基取代基的新型两亲核苷 3、5、7、9 和核碱基 12、14。大多数情况下不需要保护基团。

  DOI：

  10.1055/s-2004-831190
• 作为产物：
  描述：

  十八炔 、 8-溴膘苷 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以82%的产率得到8-(octadec-1-yn-1-yl)adenosine
  参考文献：
  名称：

  Lipophilic Nucleosides by Sonogashira Coupling

  摘要：

  通过 5-碘尿苷、8-溴腺苷和受保护的 8-溴鸟苷或相关卤代核酸的 Sonogashira 偶联，可以直接获得 N-杂环上带有亲脂性炔基取代基的新型两亲核苷 3、5、7、9 和核碱基 12、14。大多数情况下不需要保护基团。

  DOI：

  10.1055/s-2004-831190

文献信息

• Lipophilic Nucleosides by Sonogashira Coupling
  作者：Jürgen Liebscher、Wolfgang Flasche、Crina Cismas、Andreas Herrmann

  DOI：10.1055/s-2004-831190

  日期：——

  New amphiphilic nucleosides 3, 5, 7, 9 and nucleobases 12, 14, with lipophilic alkynyl substituents attached to the N-heterocyclic ring were obtained in a straightforward manner by Sonoga­shira coupling of 5-iodouridine, 8-bromoadenosine and protected 8-bromoguanosine or related halonucleobases. In most cases protective groups were unnecessary.

  通过 5-碘尿苷、8-溴腺苷和受保护的 8-溴鸟苷或相关卤代核酸的 Sonogashira 偶联，可以直接获得 N-杂环上带有亲脂性炔基取代基的新型两亲核苷 3、5、7、9 和核碱基 12、14。大多数情况下不需要保护基团。
• Design and Application of Lipophilic Nucleosides as Building Blocks to Obtain Highly Functional Biological Surfaces
  作者：Holger A. Scheidt、Wolfgang Flasche、Crina Cismas、Maximilian Rost、Andreas Herrmann、Jürgen Liebscher、Daniel Huster

  DOI：10.1021/jp046606h

  日期：2004.10.1

  For the potential application in nanobiotechnology, we have synthesized three different lipophilic nucleosides and investigated their membrane insertion and localization by solid-state NMR spectroscopy. The hydrophilic headgroups of these nucleosides consist of an adenine or uracil nucleobase, which is attached to a ribose or deoxyribose moiety. The membrane affinity of these molecules is either achieved by the covalent attachment of a 1-octadecynyl chain or an ethisterol moiety. For the first time, the orientation of these molecules and the quantitative localization of their functional groups are measured. All investigated lipophilic nucleosides can be incorporated into phospholipid membranes at high concentration without destroying the lamellar bilayer structure as shown by P-31 NMR and H-2 NMR. However, the membrane incorporation of the lipophilic nucleosides leads to modifications in the phospholipid packing properties as revealed by H-2 NMR on chain-deuterated phospholipids. Although the two nucleosides with the octadecynyl membrane anchor only impose a rather moderate decrease in phospholipid packing density, the nucleoside with a steroid membrane anchor significantly disturbs the lateral organization of the phospholipids in the membrane. Quantitative H-1 nuclear Overhauser enhancement spectroscopy under magic angle spinning conditions has been applied to localize the mono sac charide/nucleobase moiety of the nucleoside in the membrane. This method measures the intermolecular interaction strength between molecular segments. For all molecules, a location of the (deoxy)ribose/nucleobase moiety in the lipid-water interface of the membrane has been found that exposes the nucleobase to the aqueous phase, where an interaction with external molecular patterns could take place. These molecules may be useful building blocks to obtain a functionalized membrane surface that can be recognized by complementary nucleic acid strands.