8-(4-N,N-dimethylaminophenylethynyl)-2'-deoxyguanosine | 1229530-24-8

• 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-(4-N,N-dimethylaminophenylethynyl)-2'-deoxyguanosine
• 英文别名: 2-amino-8-[2-[4-(dimethylamino)phenyl]ethynyl]-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
• CAS: 1229530-24-8
• 化学式: C₂₀H₂₂N₆O₄
• 分子量: 410.432
• InChiKey: SWJRLGZNBMXUKX-SQWLQELKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  138
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(4-N,N-dimethylaminophenylethynyl)-2'-deoxyguanosine 、 N,N-二甲基甲酰胺二乙基缩醛 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到8-(4-N,N-dimethylaminophenylethynyl)-N2-(N',N'-dimethylformamidine)-2'-deoxyguanosine
  参考文献：
  名称：

  Design of environmentally sensitive fluorescent 2′-deoxyguanosine containing arylethynyl moieties: Distinction of thymine base by base-discriminating fluorescent (BDF) probe

  摘要：

  We have synthesized various substituted 8-arylethynylated 2'-deoxyguanosine derivatives. Among them, acetyl substituted deoxyguanosine analogue 4c showed a remarkable solvent dependent fluorescence property, that is, an intense fluorescence in non-polar solvents but extremely weak fluorescence in polar solvents like methanol. By using solvatofluorochromic deoxyguanosine analogue 4c, we have developed highly thymine (T) selective fluorescent DNA probes that can sense T opposite 4c in a target DNA regardless of the flanking sequences. We were able to demonstrate that 4c can be used as a T specific base-discriminating fluorescent (BDF) nucleoside in homogeneous fluorescence assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.055
• 作为产物：
  描述：

  8-ethynyl-2'-deoxyguanosine 、 4-碘-N,N-二甲基苯胺 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以50%的产率得到8-(4-N,N-dimethylaminophenylethynyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Design of environmentally sensitive fluorescent 2′-deoxyguanosine containing arylethynyl moieties: Distinction of thymine base by base-discriminating fluorescent (BDF) probe

  摘要：

  We have synthesized various substituted 8-arylethynylated 2'-deoxyguanosine derivatives. Among them, acetyl substituted deoxyguanosine analogue 4c showed a remarkable solvent dependent fluorescence property, that is, an intense fluorescence in non-polar solvents but extremely weak fluorescence in polar solvents like methanol. By using solvatofluorochromic deoxyguanosine analogue 4c, we have developed highly thymine (T) selective fluorescent DNA probes that can sense T opposite 4c in a target DNA regardless of the flanking sequences. We were able to demonstrate that 4c can be used as a T specific base-discriminating fluorescent (BDF) nucleoside in homogeneous fluorescence assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.055

文献信息

• Design of environmentally sensitive fluorescent 2′-deoxyguanosine containing arylethynyl moieties: Distinction of thymine base by base-discriminating fluorescent (BDF) probe
  作者：Yuta Shinohara、Katsuhiko Matsumoto、Kenji Kugenuma、Takashi Morii、Yoshio Saito、Isao Saito

  DOI：10.1016/j.bmcl.2010.03.055

  日期：2010.5

  We have synthesized various substituted 8-arylethynylated 2'-deoxyguanosine derivatives. Among them, acetyl substituted deoxyguanosine analogue 4c showed a remarkable solvent dependent fluorescence property, that is, an intense fluorescence in non-polar solvents but extremely weak fluorescence in polar solvents like methanol. By using solvatofluorochromic deoxyguanosine analogue 4c, we have developed highly thymine (T) selective fluorescent DNA probes that can sense T opposite 4c in a target DNA regardless of the flanking sequences. We were able to demonstrate that 4c can be used as a T specific base-discriminating fluorescent (BDF) nucleoside in homogeneous fluorescence assay. (C) 2010 Elsevier Ltd. All rights reserved.