N-[6-[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyhexyl]-2,2,2-trifluoroacetamide | 171241-19-3

• 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: N-[6-[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyhexyl]-2,2,2-trifluoroacetamide
• CAS: 171241-19-3
• 化学式: C₁₈H₂₅F₃N₆O₅
• 分子量: 462.429
• InChiKey: MFFQJNHDHTYRHL-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-[6-[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyhexyl]-2,2,2-trifluoroacetamide 在 吡啶 、 4-二甲氨基吡啶 、 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-N6-(2-phenoxyacetyl)-2'-O-(6-trifluoroacetamido)hexyladenosine
  参考文献：
  名称：

  Zwitterionic Oligonucleotides: A Study on Binding Properties of 2′-O-Aminohexyl Modifications

  摘要：

  2'-O-Aminohexyl side chains provide excellent conditions for zwitterionic interstrand and intrastrand interactions of oligonucleolides. 2'-O-Aminoalkylatedphosphoramidites of adenosine and uridine were synthesized and incorporated in increasing number into homo adenosine and homo uridine/thymidine dodecamers, respectively. CD spectra of these dodecamers with complementary sense DNA exhibited a B-DNA type structure. While duplex stability values of all tested oligonucleotides were lower than those Of the native oligonucleotides, they were significantly higher than those of 2'-O-heptyl modified oligonucleotides. The destabilization amounted to 0.9, 1.5, and 2.7 degrees C per modification for 2'-O-aminohexyl adenosine, 2'-O-aminohexyl uridine, and 2'-O-heptyl adenosine substitutions. These findings are pointing to a duplex stabilizing effect of the interaction of side chain amino groups with backbone phosphoric acid.

  DOI：

  10.1081/ncn-200067400
• 作为产物：
  描述：

  6-氨基-1-己醇 在 吡啶 、 sodium hydride 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 15.0h， 生成 N-[6-[(2R,3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyhexyl]-2,2,2-trifluoroacetamide
  参考文献：
  名称：

  Zwitterionic Oligonucleotides: A Study on Binding Properties of 2′-O-Aminohexyl Modifications

  摘要：

  2'-O-Aminohexyl side chains provide excellent conditions for zwitterionic interstrand and intrastrand interactions of oligonucleolides. 2'-O-Aminoalkylatedphosphoramidites of adenosine and uridine were synthesized and incorporated in increasing number into homo adenosine and homo uridine/thymidine dodecamers, respectively. CD spectra of these dodecamers with complementary sense DNA exhibited a B-DNA type structure. While duplex stability values of all tested oligonucleotides were lower than those Of the native oligonucleotides, they were significantly higher than those of 2'-O-heptyl modified oligonucleotides. The destabilization amounted to 0.9, 1.5, and 2.7 degrees C per modification for 2'-O-aminohexyl adenosine, 2'-O-aminohexyl uridine, and 2'-O-heptyl adenosine substitutions. These findings are pointing to a duplex stabilizing effect of the interaction of side chain amino groups with backbone phosphoric acid.

  DOI：

  10.1081/ncn-200067400