2-甲基-2-(3-苯甲酰基苯基)丙二酸 | 150360-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲基-2-(3-苯甲酰基苯基)丙二酸
• 英文名称: 2-methyl-2-(3-benzoylphenyl)malonic acid
• 英文别名: 2-(3-Benzoylphenyl)-2-methylpropanedioic acid；2-(3-benzoylphenyl)-2-methylpropanedioic acid
• CAS: 150360-24-0
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: UXAXRHKJEDCEOM-UHFFFAOYSA-N

物化性质

• 沸点：
  516.8±45.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲基-2-(3-苯甲酰基苯基)丙二酸 在 Mesorhizobium sp. BNC₁ arylmalonate decarboxylase 作用下， 生成 (2R)-2-(3-苯甲酰基苯基)丙酸
  参考文献：
  名称：

  Enantiodifferentiation of ketoprofen by Japanese firefly luciferase from Luciola lateralis

  摘要：

  Recently, we found that firefly luciferase exhibited (R)-enantioselective thioesterification activity toward 2-arylpropanoic acids. In the case of Japanese firefly luciferase from Luciola lateralis (LUG-H), the E-value for ketoprofen was approximately 20. In this study, we used a spectrophotometric method to measure the catalytic activity of LUG-H. Using this method allowed us to judge the reaction efficiency easily. Our results confirmed that LUG-H exhibits enantioselective thioesterification activity toward a series of 2-arylpropanoic acids. The highest activity was observed with ketoprofen. We also observed high enzymatic activity of LUC-H toward long-chain fatty acids. These results were reasonable because LUC-H is homologous with long-chain acyl-CoA synthetase. To obtain further information about the enantiodifferentiation mechanism of the LUC-H catalyzed thioesterification of ketoprofen, we determined the kinetic parameters of the reaction relative to each of its three substrates: ketoprofen, ATP, and coenzyme A (CoASH). We found that whereas the affinities of each compound are not affected by the chirality of ketoprofen, enantiodifferentiation is achieved by a chirality-dependent difference in the K(cat) parameter. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.01.008

文献信息

• Enantiodifferentiation of ketoprofen by Japanese firefly luciferase from Luciola lateralis
  作者：Dai-ichiro Kato、Tomohiro Tatsumi、Asami Bansho、Keisuke Teruya、Hiromitsu Yoshida、Masahiro Takeo、Seiji Negoro

  DOI：10.1016/j.molcatb.2011.01.008

  日期：2011.5

  Recently, we found that firefly luciferase exhibited (R)-enantioselective thioesterification activity toward 2-arylpropanoic acids. In the case of Japanese firefly luciferase from Luciola lateralis (LUG-H), the E-value for ketoprofen was approximately 20. In this study, we used a spectrophotometric method to measure the catalytic activity of LUG-H. Using this method allowed us to judge the reaction efficiency easily. Our results confirmed that LUG-H exhibits enantioselective thioesterification activity toward a series of 2-arylpropanoic acids. The highest activity was observed with ketoprofen. We also observed high enzymatic activity of LUC-H toward long-chain fatty acids. These results were reasonable because LUC-H is homologous with long-chain acyl-CoA synthetase. To obtain further information about the enantiodifferentiation mechanism of the LUC-H catalyzed thioesterification of ketoprofen, we determined the kinetic parameters of the reaction relative to each of its three substrates: ketoprofen, ATP, and coenzyme A (CoASH). We found that whereas the affinities of each compound are not affected by the chirality of ketoprofen, enantiodifferentiation is achieved by a chirality-dependent difference in the K(cat) parameter. (C) 2011 Elsevier B.V. All rights reserved.