N-benzoyl-3'-O-acetyl-2',5'-dideoxy-5'-iodoaristeromycin | 132019-25-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: N-benzoyl-3'-O-acetyl-2',5'-dideoxy-5'-iodoaristeromycin
• CAS: 132019-25-1
• 化学式: C₂₀H₂₀IN₅O₃
• 分子量: 505.315
• InChiKey: UMOMJQBKFPLIBY-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  99.0
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-benzoyl-3'-O-acetyl-2',5'-dideoxy-5'-iodoaristeromycin 在 吡啶 、 ammonium hydroxide 、 四氧化锇 、 sodium dithionite 、 silver fluoride 、 N-甲基吗啉氧化物 作用下， 反应 36.0h， 生成 (4'R)-2'-deoxy-4'-hydroxyaristeromycin
  参考文献：
  名称：

  Bleomycin-mediated degradation of aristeromycin-containing DNA. Novel dehydrogenation activity of ironII-bleomycin

  摘要：

  The antitumor antibiotic bleomycin (BLM) induces C-H bond scission at the C4' of deoxyribose moiety of DNA in the presence of Fe(II) and O2. To investigate the primary oxidation step, 2'-deoxyaristeromycin (Ar) possessing a cyclopentane ring instead of a ribofuranose ring was incorporated into the BLM-cleaving site of synthetic oligonucleotide d (GGArAGG). It was found that an unprecedented dehydrogenation occurs effectively at the C4' and C6' positions of the Ar moiety to give 2'-deoxyneplanocin A containing oligonucleotide together with a minor but stereospecific C4' hydroxylation in the Fe(II)-BLM-mediated degradation of duplex d(GGArAGG)-d(CCTTCC). An intermediate C4' carbocation derived from one-electron oxidation of initially formed C4' radical has been proposed for the dehydrogenation reaction.

  DOI：

  10.1021/ja00006a057
• 作为产物：
  描述：

  N-benzoyl-3'-O-acetyl-5'-O-(dimethoxytrityl)-2'-deoxyaristeromycin 在 甲基三苯氧基碘磷 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-benzoyl-3'-O-acetyl-2',5'-dideoxy-5'-iodoaristeromycin
  参考文献：
  名称：

  Bleomycin-mediated degradation of aristeromycin-containing DNA. Novel dehydrogenation activity of ironII-bleomycin

  摘要：

  The antitumor antibiotic bleomycin (BLM) induces C-H bond scission at the C4' of deoxyribose moiety of DNA in the presence of Fe(II) and O2. To investigate the primary oxidation step, 2'-deoxyaristeromycin (Ar) possessing a cyclopentane ring instead of a ribofuranose ring was incorporated into the BLM-cleaving site of synthetic oligonucleotide d (GGArAGG). It was found that an unprecedented dehydrogenation occurs effectively at the C4' and C6' positions of the Ar moiety to give 2'-deoxyneplanocin A containing oligonucleotide together with a minor but stereospecific C4' hydroxylation in the Fe(II)-BLM-mediated degradation of duplex d(GGArAGG)-d(CCTTCC). An intermediate C4' carbocation derived from one-electron oxidation of initially formed C4' radical has been proposed for the dehydrogenation reaction.

  DOI：

  10.1021/ja00006a057