6-(anthracen-9-yl)ethynyl-6-deamino-2'-deoxyadenosine

• 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: 6-(anthracen-9-yl)ethynyl-6-deamino-2'-deoxyadenosine
• 英文别名: (2R,3S,5R)-5-[6-(2-anthracen-9-ylethynyl)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• 化学式: C₂₆H₂₀N₄O₃
• 分子量: 436.47
• InChiKey: CYWRKHZJKLDECK-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(anthracen-9-yl)ethynyl-6-deamino-2'-deoxyadenosine 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 6-(anthracen-9-yl)ethynyl-3'-O-[(2-cyanoethoxy)(N,N-diisopropylamino)]phosphanyl-6-deamino-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine
  参考文献：
  名称：

  Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA

  摘要：

  Here, we report the synthesis of a hybridization probe for detection of RNA and DNA based on photoinduced electron transfer (PeT). We designed and synthesized an oligonucleotide containing an adenosine analogue with a 9-(N,N-dimethylaminomethyl)anthracenyl moiety at its 6-position via an ethynylene linker as the hybridization probe. When the probe was hybridized with a complementary RNA or DNA, the fluorescence intensity increased 3-fold or 4.5-fold, respectively, compared to the single-stranded state.

  DOI：

  10.1021/acs.joc.5b01132
• 作为产物：
  描述：

  9-氯蒽 在 bis-triphenylphosphine-palladium(II) chloride 、 双(乙腈)氯化钯(II) 、 copper(l) iodide 、 四丁基氟化铵 、 caesium carbonate 、 三乙胺 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 54.0h， 生成 6-(anthracen-9-yl)ethynyl-6-deamino-2'-deoxyadenosine
  参考文献：
  名称：

  Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA

  摘要：

  Here, we report the synthesis of a hybridization probe for detection of RNA and DNA based on photoinduced electron transfer (PeT). We designed and synthesized an oligonucleotide containing an adenosine analogue with a 9-(N,N-dimethylaminomethyl)anthracenyl moiety at its 6-position via an ethynylene linker as the hybridization probe. When the probe was hybridized with a complementary RNA or DNA, the fluorescence intensity increased 3-fold or 4.5-fold, respectively, compared to the single-stranded state.

  DOI：

  10.1021/acs.joc.5b01132

文献信息

• Photoinduced Electron-Transfer-Based Hybridization Probes for Detection of DNA and RNA
  作者：Kan Takahashi、Shun Ito、Kosuke Nakamoto、Yasutomo Ito、Yoshihito Ueno

  DOI：10.1021/acs.joc.5b01132

  日期：2015.9.4

  Here, we report the synthesis of a hybridization probe for detection of RNA and DNA based on photoinduced electron transfer (PeT). We designed and synthesized an oligonucleotide containing an adenosine analogue with a 9-(N,N-dimethylaminomethyl)anthracenyl moiety at its 6-position via an ethynylene linker as the hybridization probe. When the probe was hybridized with a complementary RNA or DNA, the fluorescence intensity increased 3-fold or 4.5-fold, respectively, compared to the single-stranded state.