trans-Cubebol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: trans-Cubebol
• 英文别名: (1S,4R,5S,6S,7R,10S)-4,10-dimethyl-7-propan-2-yltricyclo[4.4.0.01,5]decan-4-ol
• 化学式: C₁₅H₂₆O
• 分子量: 222.37
• InChiKey: KONGRWVLXLWGDV-QAIIKZMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  farnesyl pyrophosphate 在 sodium chloride 、 nickel dichloride 作用下， 以 aq. buffer 为溶剂， 生成 trans-Cubebol
  参考文献：
  名称：

  Functional Plasticity of a Viral Terpene Synthase, OILTS, that Shows Non–Specific Metal Cofactor Binding and Metal–dependent Biosynthesis

  摘要：

  OILTS is a viral class I terpene synthase found from the giant virus Orpheovirus IHUMI–LCC2. It exhibits a unique structure and demonstrates high plasticity to metal cofactors, allowing it to biosynthesize different cyclic terpene frameworks. Notably, while OILTS produces only (+)‐germacrene D–4–ol with the most common cofactor, Mg²⁺, it also biosynthesizes a different cyclic terpene, (+)‐cubebol, with Mn²⁺, Co²⁺, or Ni²⁺, presenting a rare instance of cofactor‐dependent enzyme catalysis. This is the first report of (+)‐cubebol biosynthesis, to our knowledge. In addition, OILTS can uptake Zn²⁺ as a cofactor, which is uncommon among ordinary terpene synthases. These findings suggest that OILTS′s functional plasticity may benefit the virus in diverse host environments, highlighting potential evolutionary implications.

  DOI：

  10.1002/chem.202304317