[2-13C]ubiquinone-0 | 295778-33-5

• 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: [2-13C]ubiquinone-0
• 英文别名: [2-13C]-2,3-dimethoxy-5-methyl-para-benzoquinone；2,3-dimethoxy-5-methyl(213C)cyclohexa-2,5-diene-1,4-dione
• CAS: 295778-33-5
• 化学式: C₉H₁₀O₄
• 分子量: 183.165
• InChiKey: UIXPTCZPFCVOQF-VJJZLTLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  decaprenyl bromide 、 [2-13C]ubiquinone-0 在 三氟化硼乙醚 三正丁基氢锡 、 lithium diisopropyl amide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 [6-13C]ubiquinone-10
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of [5-13C]- and [6-13C]Ubiquinone-10 for Studies of Bacterial Photosynthetic Reaction Centers

  摘要：

  This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-C-13]- and [3-C-13]ubiquinone-0 and of [5-C-13]- and [6-C-13]ubiquinone-10. A scheme based on the synthetic approach to [5-C-13]ubiquinone-10 has been worked out for the synthesis of ubiquinones C-13-labeled at any individual position and at every combination of positions in the quinone ring. The [5-C-13]- and [6-C-13]ubiquinone-10 isotopomers were incorporated into the Q(A)-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of Q(A) with a dynamic perturbation involving the 4-carbonyl functionality.

  DOI：

  10.1002/1099-0690(20021)2002:1<189::aid-ejoc189>3.0.co;2-8
• 作为产物：
  描述：

  [2-13C]-2-chloro-3-methoxy-4aα-methyl-4a,5,8,8a-tetrahydro-5α,8α-methano-1,4-naphthoquinone 在 马来酸酐 、 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 [2-13C]ubiquinone-0
  参考文献：
  名称：

  Synthesis and Spectroscopic Characterization of [5-13C]- and [6-13C]Ubiquinone-10 for Studies of Bacterial Photosynthetic Reaction Centers

  摘要：

  This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-C-13]- and [3-C-13]ubiquinone-0 and of [5-C-13]- and [6-C-13]ubiquinone-10. A scheme based on the synthetic approach to [5-C-13]ubiquinone-10 has been worked out for the synthesis of ubiquinones C-13-labeled at any individual position and at every combination of positions in the quinone ring. The [5-C-13]- and [6-C-13]ubiquinone-10 isotopomers were incorporated into the Q(A)-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of Q(A) with a dynamic perturbation involving the 4-carbonyl functionality.

  DOI：

  10.1002/1099-0690(20021)2002:1<189::aid-ejoc189>3.0.co;2-8

文献信息

• Synthesis and Spectroscopic Characterization of [5-13C]- and [6-13C]Ubiquinone-10 for Studies of Bacterial Photosynthetic Reaction Centers
  作者：Rutger B. Boers、Peter Gast、Arnold J. Hoff、Huub J. M. de Groot、Johan Lugtenburg

  DOI：10.1002/1099-0690(20021)2002:1<189::aid-ejoc189>3.0.co;2-8

  日期：2002.1

  This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-C-13]- and [3-C-13]ubiquinone-0 and of [5-C-13]- and [6-C-13]ubiquinone-10. A scheme based on the synthetic approach to [5-C-13]ubiquinone-10 has been worked out for the synthesis of ubiquinones C-13-labeled at any individual position and at every combination of positions in the quinone ring. The [5-C-13]- and [6-C-13]ubiquinone-10 isotopomers were incorporated into the Q(A)-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of Q(A) with a dynamic perturbation involving the 4-carbonyl functionality.