2-oxo-4E-hexenedioate | 167318-98-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 2-oxo-4E-hexenedioate
• 英文别名: Oxalocrotonate；(E)-5-oxohex-2-enedioic acid
• CAS: 167318-98-1
• 化学式: C₆H₆O₅
• 分子量: 158.111
• InChiKey: OOEDHTCVMHDXRH-HNQUOIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-hydroxy-2,4-hexadiene-1,6-dioate 在 NaH₂PO₄ buffer 作用下， 生成 2-oxo-4E-hexenedioate
  参考文献：
  名称：

  The Contribution of the Substrate's Carboxylate Group to the Mechanism of 4-Oxalocrotonate Tautomerase

  摘要：

  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.

  DOI：

  10.1006/bioo.1998.1095

文献信息

• Method for the Production of Glutaconate
  申请人：Zelder Oskar

  公开号：US20120021472A1

  公开（公告）日：2012-01-26

  The present invention relates to a novel method for the biocatalytic production of unsaturated dicarboxylic acids by cultivating a recombinant microorganism co-expressing a glutaconate CoA-transferase and a 2-hydroxyglutaryl-CoA dehydratase system. The present invention also relates to corresponding recombinant hosts, recombinant vectors, expression cassettes and nucleic acids suitable for preparing such hosts as well as a method of preparing polyamide or polyester copolymers making use of said dicarboxylic acids as obtained by said biocatalytic production method.

  本发明涉及一种新的生物催化生产不饱和二羧酸的方法，通过培养重组微生物共同表达谷氨酸辅酶A转移酶和2-羟基戊二酰辅酶A脱水酶系统。本发明还涉及相应的重组宿主、重组载体、表达载体和适用于制备此类宿主的核酸，以及利用所述生物催化生产方法所获得的该二羧酸制备聚酰胺或聚酯共聚物的方法。
• Hajipour, Gholamhossein; Johnson Jr., William H.; Dauben, Paul D., Journal of the American Chemical Society, 1993, vol. 115, # 9, p. 3533 - 3542
  作者：Hajipour, Gholamhossein、Johnson Jr., William H.、Dauben, Paul D.、Stolowich, Neal J.、Whitman, Christian P.

  DOI：——

  日期：——
• VERBINDUNGEN ZUR MODULATION UND ALS FUNKTIONELLER ERSATZ VON ALPHA-KETOGLUTARSÄURE (2OG)-ABHÄNGIGEN OXYGENASEN
  申请人：Homann, Thomas Melchior

  公开号：EP3762038A1

  公开（公告）日：2021-01-13
• COMPOUNDS FOR MODULATION AND AS FUNCTIONAL REPLACEMENT OF ALPHAKETOGLUTARIC ACID (2OG)-DEPENDENT OXYGENASES
  申请人：HOMANN Thomas

  公开号：US20210393677A1

  公开（公告）日：2021-12-23

  The present invention relates to an alternative co-substrate of ketoglutaric acid-dependent dioxygenases for functional production and control of same, with the aim of achieving therapeutic effects against cancer, neurodegenerative diseases and age related diseases. Epigenetically induced diseases caused by dysregulation and in particular also by metabolic dysfunction in the citric acid cycle are likewise targeted by this therapy.
• US8778645B2
  申请人：——

  公开号：US8778645B2

  公开（公告）日：2014-07-15