{(S)-2-[4-(2-Bromo-acetylamino)-phenyl]-1-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester | 76381-75-4

• 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: {(S)-2-[4-(2-Bromo-acetylamino)-phenyl]-1-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester
• CAS: 76381-75-4
• 化学式: C₂₈H₃₇BrN₈O₇
• 分子量: 677.555
• InChiKey: UFROHYIVCQZXPH-UQQWNHHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  44.0
• 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：
  193.06
• 氢给体数：
  5.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  {(S)-2-[4-(2-Bromo-acetylamino)-phenyl]-1-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 反应 5.0h， 以75%的产率得到(S)-2-Amino-3-[4-(2-bromo-acetylamino)-phenyl]-N-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-propionamide; compound with trifluoro-acetic acid
  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：

  6-(dimethylamino)-9-<3'-<amino>-3'-deoxy-β-D-ribofuranosyl>purine 在 palladium on activated charcoal ammonium hydroxide 、 氢气 、 溶剂黄146 作用下， 25.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 {(S)-2-[4-(2-Bromo-acetylamino)-phenyl]-1-[(2S,3S,4R,5R)-5-(6-dimethylamino-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester
  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