2,3-dimethoxy-5-(5-bromopentyl)-6-methyl-1,4-benzoquinone | 82413-48-7

• 英文名称: 2,3-dimethoxy-5-(5-bromopentyl)-6-methyl-1,4-benzoquinone
• 英文别名: 2-(5-bromopentyl)-3-methyl-5,6-dimethoxy-1,4-benzoquinone；6-(5-bromopentyl)ubiquinone
• CAS: 82413-48-7
• 化学式: C₁₄H₁₉BrO₄
• 分子量: 331.206
• InChiKey: JFOREYSKHPDFFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-5-(5-bromopentyl)-6-methyl-1,4-benzoquinone 在 盐酸 、 ammonium cerium (IV) nitrate 、 钾硼氢 、 双氧水 、 碘 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 9.33h， 生成 bis-6-(10-mercaptopentyl)-bisubiquinone
  参考文献：
  名称：

  Reversible Redox of NADH and NAD⁺ at a Hybrid Lipid Bilayer Membrane Using Ubiquinone

  摘要：

  Here, we report the reversible interconversion between NADH and NAD(+) at a low overpotential, which is in part mediated by ubiquinone embedded in a biomimetic membrane to mimic the initial stages of respiration. This system can be used as a platform to examine biologically relevant electroactive molecules embedded in a natural membrane environment and provide new insights into the mechanism of biological redox cycling.

  DOI：

  10.1021/ja204014s
• 作为产物：
  描述：

  6-溴己酰氯 在 双氧水 、 溶剂黄146 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 21.75h， 生成 2,3-dimethoxy-5-(5-bromopentyl)-6-methyl-1,4-benzoquinone
  参考文献：
  名称：

  Reversible Redox of NADH and NAD⁺ at a Hybrid Lipid Bilayer Membrane Using Ubiquinone

  摘要：

  Here, we report the reversible interconversion between NADH and NAD(+) at a low overpotential, which is in part mediated by ubiquinone embedded in a biomimetic membrane to mimic the initial stages of respiration. This system can be used as a platform to examine biologically relevant electroactive molecules embedded in a natural membrane environment and provide new insights into the mechanism of biological redox cycling.

  DOI：

  10.1021/ja204014s

文献信息

• Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins
  作者：Zhichao Pei、Tobias Gustavsson、Robert Roth、Torbjörn Frejd、Cecilia Hägerhäll

  DOI：10.1016/j.bmc.2010.03.075

  日期：2010.5

  Quinones are essential components in most cell and organelle bioenergetic processes both for direct electron and/or proton transfer reactions but also as means to regulate various bioenergetic processes by sensing cell redox states. To understand how quinones interact with proteins, it is important to have tools for identifying and characterizing quinone binding sites. In this work three different

  醌是大多数细胞和细胞器生物能过程中用于直接电子和/或质子转移反应的必需成分，也是通过感测细胞氧化还原状态来调节各种生物能过程的手段。要了解醌如何与蛋白质相互作用，拥有用于鉴定和表征醌结合位点的工具非常重要。在这项工作中，合成了三种不同的光反应性叠氮醌，其中两种是新型化合物，并且改进了合成方法。首先用模型肽测试叠氮醌的反应性，并通过质谱分析形成的加合物。检测到的增加的质量是各自的叠氮醌减去N 2的质量。。随后，使用三种复杂程度不同的酶系统评估了三种叠氮醌的生物活性，并研究了化合物在长波长紫外线照射下使酶失活的能力。可溶性类黄酮毒素蛋白WrbA只能使用两个叠氮醌作为底物，而呼吸链复合物I和II可以利用所有这三个化合物作为电子受体。在洗涤剂中纯化的复合物II在缺乏叠氮醌的情况下也对光照非常敏感，这使得该酶中的“治疗窗”相当狭窄。在膜结合的复合物I中，只有两种化合物使酶失活，而在第三种化合物存在下的照射使酶的活性基本不变。
• Synthesis and characterization of mitoQ and idebenone analogues as mediators of oxygen consumption in mitochondria
  作者：Damien Y. Duveau、Pablo M. Arce、Robert A. Schoenfeld、Nidhi Raghav、Gino A. Cortopassi、Sidney M. Hecht

  DOI：10.1016/j.bmc.2010.06.104

  日期：2010.9

  Analogues of mitoQ and idebenone were synthesized to define the structural elements that support oxygen consumption in the mitochondrial respiratory chain. Eight analogues were prepared and fully characterized, then evaluated for their ability to support oxygen consumption in the mitochondrial respiratory chain. While oxygen consumption was strongly inhibited by mitoQ analogues 2-4 in a chain length-dependent manner, modification of idebenone by replacement of the quinone methoxy groups by methyl groups (analogues 6-8) reduced, but did not eliminate, oxygen consumption. Idebenone analogues 6-8 also displayed significant cytoprotective properties toward cultured mammalian cells in which glutathione had been depleted by treatment with diethyl maleate. (C) 2010 Elsevier Ltd. All rights reserved.