6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine | 76494-20-7

• 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)-p-amino-L-phenylalanyl]amino}-3'-deoxy-β-D-ribofuranosyl)purine
• CAS: 76494-20-7
• 化学式: C₂₆H₃₆N₈O₆
• 分子量: 556.622
• InChiKey: NECCIKUZGQPWAF-IYRMOJGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  189.98
• 氢给体数：
  5.0
• 氢受体数：
  12.0

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， 以 1,4-二氧六环 为溶剂， 反应 72.08h， 生成 (S)-3-(4-Acetylamino-phenyl)-2-amino-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide
  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：

  N-重氮基氨基甲酸叔-丁基酯 在 palladium on activated charcoal magnesium hydroxide 、 N-羟基丁二酰亚胺 、 氢气 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 25.0~40.0 ℃ 、101.33 kPa 条件下， 反应 44.0h， 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