| 1284218-24-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1284218-24-1
• 化学式: C₁₅H₁₈N₂O₈
• 分子量: 354.317
• InChiKey: DDNLBNCFBLQLKX-FDQWZOFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.91
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  125.92
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 作用下， 反应 4.0h， 以20 mg的产率得到
  参考文献：
  名称：

  Configuration of the 5′-Methyl Group Modulates the Biophysical and Biological Properties of Locked Nucleic Acid (LNA) Oligonucleotides

  摘要：

  As part of a program aimed at exploring the structure activity relationships of 2',4'-bridged nucleic acid (BNA) containing antisense oligonucleotides (ASOs), we report the synthesis and biophysical and biological properties of R- and S-5'-Me LNA modified oligonucleotides. We show that introduction of a methyl group in the (S) configuration at the 5'-position is compatible with the high affinity recognition of complementary nucleic acids observed with LNA. In contrast, introduction of a methyl group in the (R) configuration reversed the stabilization effect of LNA. NMR studies indicated that the R-5'-Me group changes the orientation around torsion angle gamma from the +sc to the ap range at the nucleoside level, and this may in part be responsible for the poor hybridization behavior exhibited by this modification. In animal experiments, S-5'-Me-LNA, modified gapmer antisense olignucleotides showed slightly reduced potency relative to the sequence matched LNA ASOs while improving the therapeutic profile.

  DOI：

  10.1021/jm101207e