N¹-(2-nitrobenzyl)-2-azainosine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N¹-(2-nitrobenzyl)-2-azainosine
• 英文别名: 7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-[(2-nitrophenyl)methyl]imidazo[4,5-d]triazin-4-one
• 化学式: C₁₆H₁₆N₆O₇
• 分子量: 404.339
• InChiKey: BQZRJOISFVDSQG-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  179
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2',3',5'-tri-O-(acetyl)-2-azainosine 在 ammonium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 3.0h， 生成 N¹-(2-nitrobenzyl)-2-azainosine
  参考文献：
  名称：

  Synthesis and Biophysical and Biological Properties of Oligonucleotides Containing 2-Aza-2'-Deoxyinosine

  摘要：

  The preparation of oligonucleotides containing 2-aza-2'-deoxyinosine is described. Protection of the 2-azahypoxanthine moiety with the photolabile 2-nitrobenzyl group enabled us to obtain the phosphoramidite derivative and oligonucleotides containing protected 2-aza-2'-deoxyinosine. After purification, photolysis of the oligonucleotides containing the protected analogue provided the desired oligonucleotides in good yields. Melting curves of duplexes containing 2-azahypoxanthine paired with the four natural bases at pH 6 and pH 8 proved that 2-azahypoxanthine base pairs were less stable than perfectly matched duplexes but showed little variation among different bases.

  DOI：

  10.1021/jo00125a009

文献信息

• Synthesis and Biophysical and Biological Properties of Oligonucleotides Containing 2-Aza-2'-Deoxyinosine
  作者：Montse Acedo、Erik De Clercq、Ramon Eritja

  DOI：10.1021/jo00125a009

  日期：1995.10

  The preparation of oligonucleotides containing 2-aza-2'-deoxyinosine is described. Protection of the 2-azahypoxanthine moiety with the photolabile 2-nitrobenzyl group enabled us to obtain the phosphoramidite derivative and oligonucleotides containing protected 2-aza-2'-deoxyinosine. After purification, photolysis of the oligonucleotides containing the protected analogue provided the desired oligonucleotides in good yields. Melting curves of duplexes containing 2-azahypoxanthine paired with the four natural bases at pH 6 and pH 8 proved that 2-azahypoxanthine base pairs were less stable than perfectly matched duplexes but showed little variation among different bases.