O^5,6-methanocytidine | 161714-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: O^5,6-methanocytidine
• CAS: 161714-14-3
• 化学式: C₁₀H₁₃N₃O₅
• 分子量: 255.23
• InChiKey: XQLSRZULYRCHCF-ZOQUXTDFSA-N

物化性质

• 沸点：
  552.3±60.0 °C(predicted)
• 密度：
  2.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为产物：
  描述：

  2',3'-O-isopropylidene-O^5,6-methanocytidine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以65%的产率得到O^5,6-methanocytidine
  参考文献：
  名称：

  O^5′,6-Methanocytidine — Synthesis, Conformational Properties and Deamination by Cytidine Deaminase

  摘要：

  The synthesis of O-5',O-6-methanocytidine (4), a pyrimidine nucleoside restricted to the anti conformation, is described. Molecular modeling studies suggest that 4 is more flexible than conventional cyclonucleosides because of its larger-than-usual bridging system and that it can exist in a number of low energy conformations where the glycosyl rotation angles (chi) cover an similar to 80 degrees segment of the anti range. However, while both N-type (C2'-exo) and S-type (C3'-exo) sugar puckerings are possible, none of the low energy conformers adopt the C3'-endo or C2'-endo puckering modes generally seen for unconstrained nucleosides. The lowest energy conformer predicted for 4 (chi = -152 degrees, gamma = 73 degrees, P = 206 degrees) is similar to the X-ray structure of a related compound, namely 5-hydroxy-O-5',O-6-methanouridine (12, chi = -138 degrees, gamma = 63 degrees, P = 200 degrees). In solution, NMR evidence suggests an equilibrium between C2'-exo and C3'-exo puckerings for 4, and CD evidence suggests an average glycosyl rotation angle (chi) of around -160 degrees. O-5',O-6-Methano-cytidine (4) is slowly deaminated by crude cytidine deaminase from mouse liver to give O-5',O-6-methanouridine (3). Assuming that 4 interacts with the normal active site, it is concluded that cytidine deaminase from that particular source requires its ordinary substrates to adopt the anti conformation.

  DOI：

  10.1080/15257779408013214