1,8-dimethoxydehydrorabelomycin | 1403477-62-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 角环素
• 英文名称: 1,8-dimethoxydehydrorabelomycin
• 英文别名: dimethyldehydrorabelomycin；Dimethyldehydrorabelomycin；6-hydroxy-1,8-dimethoxy-3-methylbenzo[a]anthracene-7,12-dione
• CAS: 1403477-62-2
• 化学式: C₂₁H₁₆O₅
• 分子量: 348.355
• InChiKey: BQECOSITHCZNEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dehydrorabelomycin 在 S-adenosylmethioninedependent O-methyltransferase 、 S-(5'-adenosyl)-L-methionine chloride 作用下， 以 aq. phosphate buffer 为溶剂， 反应 4.0h， 以90%的产率得到1,8-dimethoxydehydrorabelomycin
  参考文献：
  名称：

  Baeyer–Villiger C–C Bond Cleavage Reaction in Gilvocarcin and Jadomycin Biosynthesis

  摘要：

  GilOII has been unambiguously identified as the key enzyme performing the crucial C-C bond cleavage reaction responsible for the unique rearrangement of a benz[a]anthracene skeleton to the benzo[d]-naphthopyranone backbone typical of the gilvocarcin-type natural anticancer antibiotics. Further investigations of this enzyme led to the isolation of a hydroxyoxepinone intermediate, leading to important conclusions regarding the cleavage mechanism.

  DOI：

  10.1021/ja3081154

文献信息

• Baeyer–Villiger C–C Bond Cleavage Reaction in Gilvocarcin and Jadomycin Biosynthesis
  作者：Nidhi Tibrewal、Pallab Pahari、Guojun Wang、Madan K. Kharel、Caleb Morris、Theresa Downey、Yanpeng Hou、Tim S. Bugni、Jürgen Rohr

  DOI：10.1021/ja3081154

  日期：2012.11.7

  GilOII has been unambiguously identified as the key enzyme performing the crucial C-C bond cleavage reaction responsible for the unique rearrangement of a benz[a]anthracene skeleton to the benzo[d]-naphthopyranone backbone typical of the gilvocarcin-type natural anticancer antibiotics. Further investigations of this enzyme led to the isolation of a hydroxyoxepinone intermediate, leading to important conclusions regarding the cleavage mechanism.