6-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-13,13,15,15-tetramethyl-9-oxa-2,4,6,14-tetrazatetracyclo[8.7.0.03,8.012,16]heptadeca-1(10),3,7,11,16-pentaen-5-one | 1393486-76-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-13,13,15,15-tetramethyl-9-oxa-2,4,6,14-tetrazatetracyclo[8.7.0.03,8.012,16]heptadeca-1(10),3,7,11,16-pentaen-5-one
• CAS: 1393486-76-4
• 化学式: C₂₂H₂₈N₄O₆
• 分子量: 444.488
• InChiKey: MCDDQSHJRLOSGZ-YWTNHNAXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-13,13,15,15-tetramethyl-9-oxa-2,4,6,14-tetrazatetracyclo[8.7.0.03,8.012,16]heptadeca-1(10),3,7,11,16-pentaen-5-one 在 4-二甲氨基吡啶 、 sodium tungstate 、 双氧水 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Synthesis and Characterization of RNA Containing a Rigid and Nonperturbing Cytidine-Derived Spin Label

  摘要：

  The nitroxide-containing nucleoside Cm is reported as the first rigid spin label for paramagnetic modification of RNA by solid-phase synthesis. The spin label is well accommodated in several RNA secondary structures as judged by its minor effect on the thermodynamic stability of hairpin and duplex RNA. Electron paramagnetic resonance (EPR) spectroscopic characterization of mono-, bi-, and trimolecular RNA structures shows that Cm will be applicable for advanced EPR studies to elucidate structural and dynamic aspects of folded RNA.

  DOI：

  10.1021/jo301227w
• 作为产物：
  描述：

  5-溴-2'-O-甲基尿苷 3',5'-二乙酸酯 在 四氯化碳 、 potassium fluoride 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 138.5h， 生成 6-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]-13,13,15,15-tetramethyl-9-oxa-2,4,6,14-tetrazatetracyclo[8.7.0.03,8.012,16]heptadeca-1(10),3,7,11,16-pentaen-5-one
  参考文献：
  名称：

  Synthesis and Characterization of RNA Containing a Rigid and Nonperturbing Cytidine-Derived Spin Label

  摘要：

  The nitroxide-containing nucleoside Cm is reported as the first rigid spin label for paramagnetic modification of RNA by solid-phase synthesis. The spin label is well accommodated in several RNA secondary structures as judged by its minor effect on the thermodynamic stability of hairpin and duplex RNA. Electron paramagnetic resonance (EPR) spectroscopic characterization of mono-, bi-, and trimolecular RNA structures shows that Cm will be applicable for advanced EPR studies to elucidate structural and dynamic aspects of folded RNA.

  DOI：

  10.1021/jo301227w

文献信息

• Synthesis and Characterization of RNA Containing a Rigid and Nonperturbing Cytidine-Derived Spin Label
  作者：Claudia Höbartner、Giuseppe Sicoli、Falk Wachowius、Dnyaneshwar B. Gophane、Snorri Th. Sigurdsson

  DOI：10.1021/jo301227w

  日期：2012.9.7

  The nitroxide-containing nucleoside Cm is reported as the first rigid spin label for paramagnetic modification of RNA by solid-phase synthesis. The spin label is well accommodated in several RNA secondary structures as judged by its minor effect on the thermodynamic stability of hairpin and duplex RNA. Electron paramagnetic resonance (EPR) spectroscopic characterization of mono-, bi-, and trimolecular RNA structures shows that Cm will be applicable for advanced EPR studies to elucidate structural and dynamic aspects of folded RNA.