5-iodo-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile | 886227-20-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 5-iodo-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile
• CAS: 886227-20-9
• 化学式: C₂₇H₅₂IN₃O₄Si₃
• 分子量: 693.889
• InChiKey: ATKCSHKNRJCZEE-GBEXAXCTSA-N

物化性质

• 沸点：
  600.4±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.06
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  78.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-iodo-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile 在 二(氰基苯)二氯化钯 、 Amberlite IRA 900 fluoride-form 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 40.0h， 生成 3-脱氮腺苷
  参考文献：
  名称：

  Efficient Ribosomal Peptidyl Transfer Critically Relies on the Presence of the Ribose 2‘-OH at A2451 of 23S rRNA

  摘要：

  The ribosomal peptidyl transferase center is a ribozyme catalyzing peptide bond synthesis in all organisms. We applied a novel modified nucleoside interference approach to identify functional groups at 9 universally conserved active site residues. Owing to their immediate proximity to the chemical center, the 23S rRNA nucleosides A2451, U2506 and U2585 were of particular interest. Our study ruled out U2506 and U2585 as contributors of vital chemical groups for transpeptidation. In contrast the ribose 2'-OH of A2451 was identified as the prime ribosomal group with potential functional importance. This 2'-OH renders almost full catalytic power to the ribosome even when embedded into an active site of six neighboring 2'-deoxyribose nucleosides. These data highlight the unique functional role of the A2451 2'-OH for peptide bond synthesis among all other functional groups at the ribosomal peptidyl transferase active site.

  DOI：

  10.1021/ja0588454
• 作为产物：
  描述：

  肌苷 在 吡啶 、 咪唑 、 二碘甲烷 、 potassium carbonate 、 乙二胺 、 对甲苯磺酰氯 、 亚硝酸异戊酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.25h， 生成 5-iodo-1-[2',3',5'-O-tris(tert-butyldimethylsilyl)-β-D-ribofuranosyl]imidazole-4-carbonitrile
  参考文献：
  名称：

  Efficient Ribosomal Peptidyl Transfer Critically Relies on the Presence of the Ribose 2‘-OH at A2451 of 23S rRNA

  摘要：

  The ribosomal peptidyl transferase center is a ribozyme catalyzing peptide bond synthesis in all organisms. We applied a novel modified nucleoside interference approach to identify functional groups at 9 universally conserved active site residues. Owing to their immediate proximity to the chemical center, the 23S rRNA nucleosides A2451, U2506 and U2585 were of particular interest. Our study ruled out U2506 and U2585 as contributors of vital chemical groups for transpeptidation. In contrast the ribose 2'-OH of A2451 was identified as the prime ribosomal group with potential functional importance. This 2'-OH renders almost full catalytic power to the ribosome even when embedded into an active site of six neighboring 2'-deoxyribose nucleosides. These data highlight the unique functional role of the A2451 2'-OH for peptide bond synthesis among all other functional groups at the ribosomal peptidyl transferase active site.

  DOI：

  10.1021/ja0588454