dimethyl ²H₂-methyl-²H₁-fumarate | 942305-24-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl ²H₂-methyl-²H₁-fumarate
• 英文别名: dimethyl (E)-2-deuterio-3-(dideuteriomethyl)but-2-enedioate
• CAS: 942305-24-0
• 化学式: C₇H₁₀O₄
• 分子量: 161.13
• InChiKey: WQEXBUQDXKPVHR-KRLGOTBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  dimethyl ²H₂-methyl-²H₁-fumarate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 30.0h， 以78%的产率得到(2-²H₁,²H₂-methyl)-mesaconic acid
  参考文献：
  名称：

  Synthesis of mono- and di-deuterated (2S,3S)-3-methylaspartic acids to facilitate measurement of intrinsic kinetic isotope effects in enzymes

  摘要：

  Kinetic isotope effects provide a powerful method to investigate the mechanisms of enzyme-catalyzed reactions, but often other slow steps in the reaction such as substrate binding or product release suppress the isotopically sensitive step. For reactions at methyl groups, this limitation may be overcomed by measuring the isotope effect by an intra-molecular competition experiment. This requires the synthesis of substrates containing regio-specifically mono- or di-deuterated methyl groups. To facilitate the mechanistic investigations of the adenosyl-cobalamin-dependent enzyme, glutamate mutase, we have developed a synthesis of mono- and di-deuterated (2S,3S)-3-methylaspartic acids. Key intermediates are the correspondingly labeled mesaconic acids and their dimethyl esters that potentially provide starting materials for a variety of isotopically labeled molecules. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.107
• 作为产物：
  描述：

  dimethyl bromo-²H₂-methyl-²H₁-fumarate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 1.0h， 以53%的产率得到dimethyl ²H₂-methyl-²H₁-fumarate
  参考文献：
  名称：

  Synthesis of mono- and di-deuterated (2S,3S)-3-methylaspartic acids to facilitate measurement of intrinsic kinetic isotope effects in enzymes

  摘要：

  Kinetic isotope effects provide a powerful method to investigate the mechanisms of enzyme-catalyzed reactions, but often other slow steps in the reaction such as substrate binding or product release suppress the isotopically sensitive step. For reactions at methyl groups, this limitation may be overcomed by measuring the isotope effect by an intra-molecular competition experiment. This requires the synthesis of substrates containing regio-specifically mono- or di-deuterated methyl groups. To facilitate the mechanistic investigations of the adenosyl-cobalamin-dependent enzyme, glutamate mutase, we have developed a synthesis of mono- and di-deuterated (2S,3S)-3-methylaspartic acids. Key intermediates are the correspondingly labeled mesaconic acids and their dimethyl esters that potentially provide starting materials for a variety of isotopically labeled molecules. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.107