N6-isobutyryl-3'-deoxyadenosine | 683241-25-0

• 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: N6-isobutyryl-3'-deoxyadenosine
• CAS: 683241-25-0
• 化学式: C₁₄H₁₉N₅O₄
• 分子量: 321.336
• InChiKey: RGOJHKROBNZUEH-ATEUNZGCSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  122.39
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N6-isobutyryl-3'-deoxyadenosine 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 72.0h， 生成 N6-isobutyryl-5'-O-4,4'-dimethoxytrityl-3'-deoxy-2'-succinatoadenosine
  参考文献：
  名称：

  Transcription inhibition using modified pentanucleotides

  摘要：

  Inhibition of gene expression was recently achieved by targeting the transcriptionally competent open complex using relatively short, pentameric modified oligonucleotides at similar to60 muM. Corroborative affinity cleavage experiments using the copper complex of a phenanthroline conjugate provided the impetus to synthesize additional analogues containing substituents at the T-position of uridine in a derivative of 5-GUGGA (-4 to +1), with the purpose of inhibiting transcription at lower concentrations. Conjugates of 5'-GUGGA modified at the T-position of uridine were convergently synthesized using a recently reported method. Seven analogues based upon the 5'-GUGGA scaffold were tested for their ability to inhibit transcription of the lac UV-5 operon. The conjugate containing a tethered pyrene showed 70% inhibition at 20 muM, and modest inhibition at as low as 5 muM. This is a significant improvement over previously tested pentanucleotides and provides direction for the preparation of a next generation of inhibitors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00071-3
• 作为产物：
  描述：

  虫草素 、 异丁酰氯 在 吡啶 、 三甲基氯硅烷 、 氟化铵 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 5.0h， 以8%的产率得到N6-isobutyryl-3'-deoxyadenosine
  参考文献：
  名称：

  Transcription inhibition using modified pentanucleotides

  摘要：

  Inhibition of gene expression was recently achieved by targeting the transcriptionally competent open complex using relatively short, pentameric modified oligonucleotides at similar to60 muM. Corroborative affinity cleavage experiments using the copper complex of a phenanthroline conjugate provided the impetus to synthesize additional analogues containing substituents at the T-position of uridine in a derivative of 5-GUGGA (-4 to +1), with the purpose of inhibiting transcription at lower concentrations. Conjugates of 5'-GUGGA modified at the T-position of uridine were convergently synthesized using a recently reported method. Seven analogues based upon the 5'-GUGGA scaffold were tested for their ability to inhibit transcription of the lac UV-5 operon. The conjugate containing a tethered pyrene showed 70% inhibition at 20 muM, and modest inhibition at as low as 5 muM. This is a significant improvement over previously tested pentanucleotides and provides direction for the preparation of a next generation of inhibitors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00071-3