5'-O-benzhydryloxy-bis(trimethylsilyloxy)silyl-N⁴,2'-O-dimethylcytidine | 1431457-37-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-benzhydryloxy-bis(trimethylsilyloxy)silyl-N⁴,2'-O-dimethylcytidine
• CAS: 1431457-37-2
• 化学式: C₃₀H₄₅N₃O₈Si₃
• 分子量: 659.959
• InChiKey: VUYVNCUVONWXCO-BRLXWGKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  44.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  122.53
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5'-O-benzhydryloxy-bis(trimethylsilyloxy)silyl-N⁴,2'-O-dimethylcytidine 、 bis(N,N-diisopropylamino)methoxyphosphine 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以75%的产率得到5'-O-benzhydryloxy-bis(trimethylsilyloxy)silyl-3'-O-(N,N-diisopropylamino)methoxyphosphonyl-N⁴,2'-O-dimethylcytidine
  参考文献：
  名称：

  Probing the stabilizing effects of modified nucleotides in the bacterial decoding region of 16S ribosomal RNA

  摘要：

  The bacterial decoding region of 16S ribosomal RNA has multiple modified nucleotides. In order to study the role of N-4,2'-O-dimethylcytidine (m(4)Cm), the corresponding phosphoramidite was synthesized utilizing 5'-silyl-2'-ACE chemistry. Using solid-phase synthesis, m(4)Cm, 5-methylcytidine (m(5)C), 3-methyluridine (m(3)U), and 2'-O-methylcytidine (Cm) were site-specifically incorporated into small RNAs representing the decoding regions of different bacterial species. Biophysical studies were then used to provide insight into the stabilizing roles of the modified nucleotides. These studies reveal that methylation of cytidine and uridine has different effects. The same modifications at different positions or sequence contexts within similar RNA constructs also have contrasting roles, such as stabilizing or destabilizing the RNA helix. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.010
• 作为产物：
  描述：

  N⁴,2′-O-dimethylcytidine 、 二苯甲基氧基双(三甲基甲硅烷基氧基)氯硅烷 在 二异丙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以80%的产率得到5'-O-benzhydryloxy-bis(trimethylsilyloxy)silyl-N⁴,2'-O-dimethylcytidine
  参考文献：
  名称：

  Probing the stabilizing effects of modified nucleotides in the bacterial decoding region of 16S ribosomal RNA

  摘要：

  The bacterial decoding region of 16S ribosomal RNA has multiple modified nucleotides. In order to study the role of N-4,2'-O-dimethylcytidine (m(4)Cm), the corresponding phosphoramidite was synthesized utilizing 5'-silyl-2'-ACE chemistry. Using solid-phase synthesis, m(4)Cm, 5-methylcytidine (m(5)C), 3-methyluridine (m(3)U), and 2'-O-methylcytidine (Cm) were site-specifically incorporated into small RNAs representing the decoding regions of different bacterial species. Biophysical studies were then used to provide insight into the stabilizing roles of the modified nucleotides. These studies reveal that methylation of cytidine and uridine has different effects. The same modifications at different positions or sequence contexts within similar RNA constructs also have contrasting roles, such as stabilizing or destabilizing the RNA helix. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.010