2-[(2,3-Dimethyl-5-methylidene-4-oxocyclopent-2-en-1-yl)methyl]-4,5-dimethylcyclopent-4-ene-1,3-dione | 1254558-03-6

• 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: 2-[(2,3-Dimethyl-5-methylidene-4-oxocyclopent-2-en-1-yl)methyl]-4,5-dimethylcyclopent-4-ene-1,3-dione
• 英文别名: 2-[(2,3-dimethyl-5-methylidene-4-oxocyclopent-2-en-1-yl)methyl]-4,5-dimethylcyclopent-4-ene-1,3-dione
• CAS: 1254558-03-6
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: LTWZSFYXGKAWCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(2,3-Dimethyl-5-methylidene-4-oxocyclopent-2-en-1-yl)methyl]-4,5-dimethylcyclopent-4-ene-1,3-dione 在 Streptomyces coelicolor cytochrome P₄₅₀ 154A₁ 作用下， 反应 3.0h， 生成
  参考文献：
  名称：

  Cyclization of a Cellular Dipentaenone by Streptomyces coelicolor Cytochrome P450 154A1 without Oxidation/Reduction

  摘要：

  We report a comprehensive genetic, metabolomic, and biochemical study on the catalytic properties of Streptomyces coelicolor cytochrome P450 (P450) 154A1, known to have a unique heme orientation in its crystal structure. Deletion of the P450 154A1 gene compromised the long-term stability of the bacterial spores. A novel dipentaenone (1) with a high degree of conjugation was identified as an endogenous substrate of P450 154A1 using a metabolomics approach. The biotransformation of 1 by P450 154A1 was shown to be an unexpected intramolecular cyclization to a Paterno-Buchi-like product, without oxidation/reduction.

  DOI：

  10.1021/ja107801v

文献信息

• Cyclization of a Cellular Dipentaenone by <i>Streptomyces coelicolor</i> Cytochrome P450 154A1 without Oxidation/Reduction
  作者：Qian Cheng、David C. Lamb、Steven L. Kelly、Li Lei、F. Peter Guengerich

  DOI：10.1021/ja107801v

  日期：2010.11.3

  We report a comprehensive genetic, metabolomic, and biochemical study on the catalytic properties of Streptomyces coelicolor cytochrome P450 (P450) 154A1, known to have a unique heme orientation in its crystal structure. Deletion of the P450 154A1 gene compromised the long-term stability of the bacterial spores. A novel dipentaenone (1) with a high degree of conjugation was identified as an endogenous substrate of P450 154A1 using a metabolomics approach. The biotransformation of 1 by P450 154A1 was shown to be an unexpected intramolecular cyclization to a Paterno-Buchi-like product, without oxidation/reduction.