(E)-8-(4-acetylstyryl)-2'-deoxyguanosine | 1277165-50-0

• 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: (E)-8-(4-acetylstyryl)-2'-deoxyguanosine
• 英文别名: (E)-8-styryl-deoxyguanosine；8-[(E)-2-(4-acetylphenyl)ethenyl]-2-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 1277165-50-0
• 化学式: C₂₀H₂₁N₅O₅
• 分子量: 411.417
• InChiKey: KGNNUODXITWKQO-OQIUDGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  8-溴-2'-脱氧鸟苷 在 ammonium hydroxide 、 四(三苯基膦)钯 、 sodium acetate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (E)-8-(4-acetylstyryl)-2'-deoxyguanosine
  参考文献：
  名称：

  Design and synthesis of highly solvatochromic fluorescent 2′-deoxyguanosine and 2′-deoxyadenosine analogs

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.11.129

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.