1-epi-3-Dehydroquinic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 1-epi-3-Dehydroquinic acid
• 英文别名: (1S,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid
• 化学式: C₇H₁₀O₆
• 分子量: 190.153
• InChiKey: WVMWZWGZRAXUBK-BYHIOWSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  右旋奎宁酸 在 palladium on activated charcoal 咪唑 、 草酰氯 、 硫酸 、 氢氟酸 、 氢气 、 乙酸酐 、 potassium carbonate 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 153.58h， 生成 1-epi-3-Dehydroquinic acid
  参考文献：
  名称：

  Divergence between the enzyme-catalyzed and noncatalyzed synthesis of 3-dehydroquinate

  摘要：

  Synthesis of 1-epi-debydroquinate, 9, provided an authentic sample of this material and allowed its identification as a minor product in the noncatalyzed rearrangement of enolpyranose 4a to 3-dehydroquinate, 7 (3-DHQ). None of this isomer was detected in the product of the transformation of DAHP, 1 to 3-DHQ catalyzed by dehydroquinate synthase. This result indicates that the enolpyranose 4a is not released from the enzyme active site prior to rearrangement to 3-DHQ, a possibility suggested previously (Bartlett, P.A.; Satake, K. J. Am. Chem. Sec, 1988, 110, 1628-1630). Enolpyranose 4a was generated in the presence of DHQ synthase; however, the formation of 9 was not diminished, indicating that spontaneous rearrangement is faster than uptake by the enzyme under these conditions. The question remains whether the enzyme takes an active role in catalyzing the rearrangement of 4a to 3-DHQ or simply provides a conformational template to prevent formation of the side product 9,

  DOI：

  10.1021/jo00087a024

文献信息

• Divergence between the enzyme-catalyzed and noncatalyzed synthesis of 3-dehydroquinate
  作者：Paul A. Bartlett、Kevin L. McLaren、Matthew A. Marx

  DOI：10.1021/jo00087a024

  日期：1994.4

  Synthesis of 1-epi-debydroquinate, 9, provided an authentic sample of this material and allowed its identification as a minor product in the noncatalyzed rearrangement of enolpyranose 4a to 3-dehydroquinate, 7 (3-DHQ). None of this isomer was detected in the product of the transformation of DAHP, 1 to 3-DHQ catalyzed by dehydroquinate synthase. This result indicates that the enolpyranose 4a is not released from the enzyme active site prior to rearrangement to 3-DHQ, a possibility suggested previously (Bartlett, P.A.; Satake, K. J. Am. Chem. Sec, 1988, 110, 1628-1630). Enolpyranose 4a was generated in the presence of DHQ synthase; however, the formation of 9 was not diminished, indicating that spontaneous rearrangement is faster than uptake by the enzyme under these conditions. The question remains whether the enzyme takes an active role in catalyzing the rearrangement of 4a to 3-DHQ or simply provides a conformational template to prevent formation of the side product 9,