(3S,6R)-2,5-dimethoxy-3-((2'R)-methoxypropionyl)-6-isopropyl-3,6-dihydropyrazine

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (3S,6R)-2,5-dimethoxy-3-((2'R)-methoxypropionyl)-6-isopropyl-3,6-dihydropyrazine
• 英文别名: methyl (2R)-2-[(2S,5R)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]propanoate
• 化学式: C₁₃H₂₂N₂O₄
• 分子量: 270.329
• InChiKey: FECMXSIEFWAVIL-BBBLOLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  69.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,6R)-2,5-dimethoxy-3-((2'R)-methoxypropionyl)-6-isopropyl-3,6-dihydropyrazine 在 盐酸 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 D-缬氨酸甲酯盐酸盐 、 (2S,3R)-dimethyl-3-methylaspartic acid hydrochloride
  参考文献：
  名称：

  Syntheses of (2S,3R)- and (2S,3R)[3-2h]- 3-methylaspartic acid: slow substrates for a syn-elimination reaction catalysed by methylaspartase.

  摘要：

  Mediylaspartase catalyses the slow syn-elimination of ammonia from the (2S,3R)-[L-erythro]-diastereomer of the natural substrate, (2S,3S)-3-methylaspartic acid, to give mesaconic acid. To provide material of sufficient stereochemical purity to probe the mechanism of the reaction, two synthetic routes to (2S,3R)- and (2S,3R)[3-H-2]- 3-methylaspartic acid were devised. The use of these (2S,3R)-3-methylaspartic acids revealed that the enzymic reaction does not involve C-3 epimerisation followed by normal anti-elimination, ruling-out the possibility of a carbanion intermediate. Conversely, the substrate displayed very large primary deuterium isotope effects indicating rate-limiting C-H bond cleavage.

  DOI：

  10.1016/s0957-4166(00)80221-9
• 作为产物：
  描述：

  甲基(2R)-2-溴丙酸酯 、 (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 正丁基锂 作用下， 生成 1-(3,6-Dimethoxy-5-propan-2-ylpyrazin-2-yl)propan-1-one 、 (3S,6R)-2,5-dimethoxy-3-((2'R)-methoxypropionyl)-6-isopropyl-3,6-dihydropyrazine
  参考文献：
  名称：

  Syntheses of (2S,3R)- and (2S,3R)[3-2h]- 3-methylaspartic acid: slow substrates for a syn-elimination reaction catalysed by methylaspartase.

  摘要：

  Mediylaspartase catalyses the slow syn-elimination of ammonia from the (2S,3R)-[L-erythro]-diastereomer of the natural substrate, (2S,3S)-3-methylaspartic acid, to give mesaconic acid. To provide material of sufficient stereochemical purity to probe the mechanism of the reaction, two synthetic routes to (2S,3R)- and (2S,3R)[3-H-2]- 3-methylaspartic acid were devised. The use of these (2S,3R)-3-methylaspartic acids revealed that the enzymic reaction does not involve C-3 epimerisation followed by normal anti-elimination, ruling-out the possibility of a carbanion intermediate. Conversely, the substrate displayed very large primary deuterium isotope effects indicating rate-limiting C-H bond cleavage.

  DOI：

  10.1016/s0957-4166(00)80221-9

文献信息

• Syntheses of (2S,3R)- and (2S,3R)[3-2h]- 3-methylaspartic acid: slow substrates for a syn-elimination reaction catalysed by methylaspartase.
  作者：Catherine H. Archer、Neil R. Thomas、David Gani

  DOI：10.1016/s0957-4166(00)80221-9

  日期：1993.6

  Mediylaspartase catalyses the slow syn-elimination of ammonia from the (2S,3R)-[L-erythro]-diastereomer of the natural substrate, (2S,3S)-3-methylaspartic acid, to give mesaconic acid. To provide material of sufficient stereochemical purity to probe the mechanism of the reaction, two synthetic routes to (2S,3R)- and (2S,3R)[3-H-2]- 3-methylaspartic acid were devised. The use of these (2S,3R)-3-methylaspartic acids revealed that the enzymic reaction does not involve C-3 epimerisation followed by normal anti-elimination, ruling-out the possibility of a carbanion intermediate. Conversely, the substrate displayed very large primary deuterium isotope effects indicating rate-limiting C-H bond cleavage.