2-hydroxy-2,4Z-heptadiene-1,7-dioate | 167319-01-9

• 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: 2-hydroxy-2,4Z-heptadiene-1,7-dioate
• 英文别名: (2Z,4Z)-2-hydroxyhepta-2,4-dienedioic acid
• CAS: 167319-01-9
• 化学式: C₇H₈O₅
• 分子量: 172.138
• InChiKey: ZBCBETMBSDTINL-NWJCXACMSA-N

物化性质

• 沸点：
  520.0±50.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2,4Z-heptadiene-1,7-dioate 在 sodium dihydrogenphosphate 、 甲酸 、 2-oxo-hept-4-ene-1,7-dioate hydratase 、 Dowex-1 (formate) exchange resin 、 双氧水 、 magnesium chloride 、 catalase 作用下， 以 氘代二甲亚砜 为溶剂， 反应 0.27h， 生成 v-Carboxymethylbutanolid
  参考文献：
  名称：

  2-Oxo-hept-4-ene-1,7-dioate 水合酶的立体化学和同位素标记研究：水合反应中酶催化酮化步骤的证据

  摘要：

  来自大肠杆菌 C 的 2-Oxo-hept-4-ene-1,7-dioate 水合酶将 2-oxo-hept-4-ene-1,7-dioate 转化为 2-oxo-4-hydroxy-hepta-1,7 -通过使用镁作为辅助因子添加水来添加-dioate。该酶是一组可诱导酶中的一种，统称为同原儿茶酸元裂变途径。整个途径使生物体能够利用芳香族氨基酸作为其唯一的碳和能量来源。2-oxo-hept-4-ene-1,7-dioate hydratase 的表达和纯化至均一性允许动力学、同位素标记和立体化学研究。动力学研究表明，该酶可以用相当的设备将 2-oxo-hept-4-ene-1,7-dioate 或 2-hydroxy-2,4-heptadiene-1,7-dioate 加工成产品。同位素标记研究表明，当反应在 2H2O 中进行时，水合酶催化 C-3 和 C-5 处溶剂氘的掺入。该酶还加速了替代底物

  DOI：

  10.1021/ja9808402
• 作为产物：
  描述：

  5-(carboxymethyl)-2-hydroxymuconic acid 在 NaH₂PO₄ buffer 、 碳酸氢钠 作用下， 以25%的产率得到2-hydroxy-2,4Z-heptadiene-1,7-dioate
  参考文献：
  名称：

  Johnson; Hajipour; Whitman, Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8719 - 8726

  摘要：

  DOI：

文献信息

• The Contribution of the Substrate's Carboxylate Group to the Mechanism of 4-Oxalocrotonate Tautomerase
  作者：Huiling Lian、Robert M. Czerwinski、Thanuja M. Stanley、William H. Johnson、Robert J. Watson、Christian P. Whitman

  DOI：10.1006/bioo.1998.1095

  日期：1998.10

  4-Oxalocrotonate tautomerase (4-OT) converts 2-oxo-4E-hexenedioate (1) to 2-oxo-3E-hexenedioate (3) through the dienol intermediate, 2-hydroxy-2,4-hexadiene-1,6-dioate (2). Previous studies established that the isomerization of 1 to 3 is primarily a suprafacial process. It was also suggested that the 6-carboxylate group of the substrate maintains the regio- and stereochemical fidelity of the reaction by anchoring the substrate at the active site. A subsequent study suggested an additional role for the 6-carboxylate group in the mechanism: the enzyme may utilize the binding energy of the carboxylate group to facilitate catalysis. In order to explore the role of the carboxylate group in the mechanism further, the nonenzymatic rate constants for mono- and dicarboxylated substrates were measured and compared to the rates obtained for the corresponding enzymatic reactions. The results show that the missing carboxylate group has a profound effect on enzymatic catalysis as evidenced by the significant decreases (a 10(4)- and a 10(5)-fold reduction) in the values of k(cat)/K-m observed for the two monocarboxylated substrates. A comparison of the nonenzymatic rate constants indicates that the reduced k(cat)/K-m values cannot be explained on the basis of the chemical reactivities. The stereochemical course of the 4-OT-catalyzed reaction was also determined using 2-hydroxy-2,4Z-heptadiene-1,7-dioate. The stereochemical analysis reveals that the presence of the carboxylate group improves the stereoselectivity of the enzyme-catalyzed ketonization of 2-hydroxy-2,4Z-heptadiene-1,7-dioate to 2-oxo-[3-H-2]-4Z-heptene-1,7-dioate in (H2O)-H-2-a result that is consistent with its previously assigned role. These findings provide further evidence that the substrate's carboxylate group contributes to the mechanism of the enzyme in two ways: it anchors the substrate at the active site and it facilitates catalysis by destabilizing the substrate or by stabilizing the transition state. (C) 1998 Academic Press.
• Stereochemical and Isotopic Labeling Studies of 2-Oxo-hept-4-ene-1,7-dioate Hydratase:  Evidence for an Enzyme-Catalyzed Ketonization Step in the Hydration Reaction
  作者：Elizabeth A. Burks、William H. Johnson、Christian P. Whitman

  DOI：10.1021/ja9808402

  日期：1998.8.1

  permitted kinetic, isotopic labeling, and stereochemical studies. Kinetic studies show that the enzyme processes either 2-oxo-hept-4-ene-1,7-dioate or 2-hydroxy-2,4-heptadiene-1,7-dioate to product with comparable facility. Isotope labeling studies show that the hydratase catalyzes the incorporation of a solvent deuteron at both C-3 and C-5 when the reaction is performed in 2H2O. The enzyme also accelerates

  来自大肠杆菌 C 的 2-Oxo-hept-4-ene-1,7-dioate 水合酶将 2-oxo-hept-4-ene-1,7-dioate 转化为 2-oxo-4-hydroxy-hepta-1,7 -通过使用镁作为辅助因子添加水来添加-dioate。该酶是一组可诱导酶中的一种，统称为同原儿茶酸元裂变途径。整个途径使生物体能够利用芳香族氨基酸作为其唯一的碳和能量来源。2-oxo-hept-4-ene-1,7-dioate hydratase 的表达和纯化至均一性允许动力学、同位素标记和立体化学研究。动力学研究表明，该酶可以用相当的设备将 2-oxo-hept-4-ene-1,7-dioate 或 2-hydroxy-2,4-heptadiene-1,7-dioate 加工成产品。同位素标记研究表明，当反应在 2H2O 中进行时，水合酶催化 C-3 和 C-5 处溶剂氘的掺入。该酶还加速了替代底物
• Johnson; Hajipour; Whitman, Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8719 - 8726
  作者：Johnson、Hajipour、Whitman

  DOI：——

  日期：——