α-1,N(6)ethenodeoxyadenosine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: α-1,N(6)ethenodeoxyadenosine
• 英文别名: (2R,3S,5S)-2-(Hydroxymethyl)-5-(3H-imidazo[2,1-i]purin-3-yl)tetrahydrofuran-3-ol；(2R,3S,5S)-2-(hydroxymethyl)-5-imidazo[2,1-f]purin-3-yloxolan-3-ol
• 化学式: C₁₂H₁₃N₅O₃
• 分子量: 275.267
• InChiKey: XQQIMTUYVDUWKJ-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  97.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氯乙醛 、 α-deoxyadenosine 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 72.0h， 以60%的产率得到α-1,N(6)ethenodeoxyadenosine
  参考文献：
  名称：

  Fluorescent α-Anomeric 1,N(6)Etheno- Deoxyadenosine in DNA Duplexes. the α-εdA / dG Pair

  摘要：

  Structural properties of the fluorescent alpha -anomeric 1,N(6)ethenodeoxyadenosine residue placed in opposition to all four canonical deoxynucleotide units within 11-mer DNA duplexes have been studied. The duplex with alpha-epsilon dA / dG pairing is most thermodynamically stable while the alpha-epsilon dA/dC one is the least stable. Fluorescence measurements confirm. the thermodynamic data and indicate base-pair dependent stacking properties of alpha-epsilon dA within duplex structures. Results of molecular dynamics (MD) simulations in aqueous solution for the most stable duplex point to the presence of different conformational states of the alpha -1,N(6)etheno-deoxyadenosine residue, including formation of a hydrogen bonded pair with the dG and possible occurrence of severe kinking in the duplex.

  DOI：

  10.1080/15257770008045456

文献信息

• Fluorescent α-Anomeric 1,N(6)Etheno- Deoxyadenosine in DNA Duplexes. the α-εdA / dG Pair
  作者：L. Bielecki、B. Skalski、I. Zagórowska、R. E. Verrall、R. W. Adamiak

  DOI：10.1080/15257770008045456

  日期：2000.10

  Structural properties of the fluorescent alpha -anomeric 1,N(6)ethenodeoxyadenosine residue placed in opposition to all four canonical deoxynucleotide units within 11-mer DNA duplexes have been studied. The duplex with alpha-epsilon dA / dG pairing is most thermodynamically stable while the alpha-epsilon dA/dC one is the least stable. Fluorescence measurements confirm. the thermodynamic data and indicate base-pair dependent stacking properties of alpha-epsilon dA within duplex structures. Results of molecular dynamics (MD) simulations in aqueous solution for the most stable duplex point to the presence of different conformational states of the alpha -1,N(6)etheno-deoxyadenosine residue, including formation of a hydrogen bonded pair with the dG and possible occurrence of severe kinking in the duplex.