5'-O-(4,4'-dimethoxytrityl)-1,3,2',6'-tetra-N-trifluoroacetylribostamycin | 1315508-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5'-O-(4,4'-dimethoxytrityl)-1,3,2',6'-tetra-N-trifluoroacetylribostamycin
• CAS: 1315508-28-1
• 化学式: C₄₆H₄₈F₁₂N₄O₁₆
• 分子量: 1140.89
• InChiKey: CIIPQAJHFUXIHF-ZIMPPOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  78.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  282.16
• 氢给体数：
  9.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  核糖霉素 在 吡啶 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 5'-O-(4,4'-dimethoxytrityl)-1,3,2',6'-tetra-N-trifluoroacetylribostamycin
  参考文献：
  名称：

  Synthesis of Aminoglycoside-3′-Conjugates of 2′-O-Methyl Oligoribonucleotides and Their Invasion to a ¹⁹F labeled HIV-1 TAR Model

  摘要：

  The potential of aminoglycosides to induce RNA-invasion has been demonstrated. For this purpose, aminoglycoside-3'-conjugates of 2'-O-methyl oligoribonucleotides have been synthesized entirely on a solid phase. The synthesis includes an automated oligonucleotide chain elongation to solid-supported neomycin, ribostamycin, and methyl neobiosamine, and a two-step deprotection/release of the solid-supported conjugate, which allows exploitation of a simple protecting group scheme. Conjugates have been targeted to a F-19 labeled HIV-1 TAR RNA model (Trans Activation Response element of HIV), which allows monitoring of the invasion by F-19 NMR spectroscopy. A remarkably enhanced invasion, compared to that resulting from the corresponding unmodified 2'-O-methyl oligoribonucleotide (5'-CAGGCUCA-3'), has been obtained by the neomycin conjugate. The increased affinity results from a cooperative binding of the neomycin moiety and hybridization, though the invasion may also follow a mechanism, in which the first molar equivalent of the conjugate induces hybridization of the second.

  DOI：

  10.1021/bc200101r