(Z)-8-styryl-2'-deoxyguanosine | 1024597-42-9

• 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: (Z)-8-styryl-2'-deoxyguanosine
• 英文别名: 2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-[(Z)-2-phenylethenyl]-1H-purin-6-one
• CAS: 1024597-42-9
• 化学式: C₁₈H₁₉N₅O₄
• 分子量: 369.38
• InChiKey: QMBRQDHODNDMLA-TWAAFDNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  8-phenylethynyl-2'-deoxyguanosine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以40%的产率得到(Z)-8-styryl-2'-deoxyguanosine
  参考文献：
  名称：

  Synthesis and reversible photoisomerization of photoswitchable nucleoside, 8-styryl-2′-deoxyguanosine

  摘要：

  A novel guanosine derivative with a photoswitching property, 8-styryl-2'-deoxyguanosine was synthesized, and showed very rapid and efficient reversible E-Z photoisomerization upon illumination at specific wavelength. In addition, E-Z photoisomerization can be iteratively performed by alternate illumination with monochroic 254 nm and 370 nm light without any side reactions. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.124

文献信息

• Design and synthesis of highly solvatochromic fluorescent 2′-deoxyguanosine and 2′-deoxyadenosine analogs
  作者：Katsuhiko Matsumoto、Naoya Takahashi、Azusa Suzuki、Takashi Morii、Yoshio Saito、Isao Saito

  DOI：10.1016/j.bmcl.2010.11.129

  日期：2011.2

  We synthesized various substituted 8-styryl-2'-deoxyguanosine and 8-styryl-2'-deoxyadenosine derivatives. Among them only acetyl substituted 8-styryl-2'-deoxyguanosine analog 5b showed a remarkable solvatochromicity (Delta lambda(em)(max) = 91 nm), that is, strong fluorescence at 477 nm in 1,4-dioxane, but in methanol the fluorescence was red shifted to 558 nm with very low intensity. Such environmentally sensitive solvatochromic fluorescent guanosine analogs may be useful as a sensor for investigating interactions of DNA with DNA binding proteins. (C) 2010 Elsevier Ltd. All rights reserved.