N¹-(2-nitrobenzyl)-2-aza-2'-deoxyinosine | 170373-80-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N¹-(2-nitrobenzyl)-2-aza-2'-deoxyinosine
• 英文别名: 7-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3-[(2-nitrophenyl)methyl]imidazo[4,5-d]triazin-4-one
• CAS: 170373-80-5
• 化学式: C₁₆H₁₆N₆O₆
• 分子量: 388.34
• InChiKey: PQTBTUFOKXIBRS-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  28
• 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：
  158
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N¹-(2-nitrobenzyl)-2-aza-2'-deoxyinosine 在 N,N-二异丙基乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 3'-O-<(2-cyanoethoxy)-(N,N-diisopropylamino)phosphinyl>-5'-O-(dimethoxytrityl)-N¹-(2-nitrobenzyl)-2-aza-2'-deoxyinosine
  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
• 作为产物：
  描述：

  3',5'-O-tetraisopropyldisiloxane-1,3-diyl-2-azainosine 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 、 乙腈 为溶剂， 反应 8.25h， 生成 N¹-(2-nitrobenzyl)-2-aza-2'-deoxyinosine
  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.