6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine | 76381-71-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine
• 英文别名: 6-(dimethylamino)-9-(3'-{[N-(tert-butyloxycarbonyl)-4-azido-2-nitro-L-phenylalanyl]amino}-3'-deoxy-β-D-ribofuranosyl)purine
• CAS: 76381-71-0
• 化学式: C₂₆H₃₃N₁₁O₈
• 分子量: 627.617
• InChiKey: WFGBWTXPHOEMFP-MILYTXAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  45.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  255.86
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine 在 三氟乙酸 作用下， 反应 0.22h， 以36%的产率得到6-(dimethylamino)-9-<3'-<(4-azido-2-nitro-L-phenylalanyl)amino>-3'-deoxy-β-D-ribofuranosyl>purine
  参考文献：
  名称：

  Puromycin analogs. Effect of aryl-substituted puromycin analogs on the ribosomal peptidyltransferase reaction

  摘要：

  A series of ortho- and para-substituted L-phenylalanylpuromycin analogues were synthesized and evaluated as substrates for the peptidyltransferase reaction of Escherichia coli ribosomes. Kinetic results reveal that substitution of the p-methoxy group of the puromycin molecule alters the peptidyltransferase activity of the molecule with the following decreasing order of substrate efficiencies: p-NH2 greater than p-NHCOCH3 greater than p-NO2 = p-NHCO(CH2)2CH3 greater than p-NHCOCH2Br. However, the inability of the ribosome to tolerate a nitro group at the ortho position of the phenylalanine ring precluded the use of the photosensitive puromycin analogue, 2-nitro-4-azidophenylalanylpuromycin aminonucleoside (7a), as a photoaffinity label for the peptidyltransferase site.

  DOI：

  10.1021/jm00135a013
• 作为产物：
  描述：

  p-Azido-o-nitrophenylalanin 在 sodium hydroxide 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 1,4-二氧六环 、 乙醇 、 氯仿 为溶剂， 反应 5.0h， 生成 6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine
  参考文献：
  名称：

  Puromycin analogs. Effect of aryl-substituted puromycin analogs on the ribosomal peptidyltransferase reaction

  摘要：

  A series of ortho- and para-substituted L-phenylalanylpuromycin analogues were synthesized and evaluated as substrates for the peptidyltransferase reaction of Escherichia coli ribosomes. Kinetic results reveal that substitution of the p-methoxy group of the puromycin molecule alters the peptidyltransferase activity of the molecule with the following decreasing order of substrate efficiencies: p-NH2 greater than p-NHCOCH3 greater than p-NO2 = p-NHCO(CH2)2CH3 greater than p-NHCOCH2Br. However, the inability of the ribosome to tolerate a nitro group at the ortho position of the phenylalanine ring precluded the use of the photosensitive puromycin analogue, 2-nitro-4-azidophenylalanylpuromycin aminonucleoside (7a), as a photoaffinity label for the peptidyltransferase site.

  DOI：

  10.1021/jm00135a013