(E)-2-Oxo-hept-3-enedioic acid

• 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: (E)-2-Oxo-hept-3-enedioic acid
• 英文别名: trans-2-Oxohept-3-enedioic acid；(E)-2-oxohept-3-enedioic acid
• 化学式: C₇H₈O₅
• 分子量: 172.138
• InChiKey: HYVSZVZMTYIHKF-HNQUOIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 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-2,4Z-heptadiene-1,7-dioate 在 NaH₂PO₄ buffer 作用下， 生成 (E)-2-Oxo-hept-3-enedioic acid
  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

• BIOLOGICAL SYNTHESIS OF DIFUNCTIONAL HEXANES AND PENTANES FROM CARBOHYDRATE FEEDSTOCKS
  申请人：Baynes Brian M.

  公开号：US20120301950A1

  公开（公告）日：2012-11-29

  Provided herein are methods for the production of difunctional alkanes in microorganisms. Also provided are enzymes and nucleic acids encoding such enzymes, associated with the difunctional alkane production from carbohydrates feedstocks in microorganisms. The invention also provides recombinant microorganisms and metabolic pathways for the production of difunctional alkanes.

  本文提供了在微生物中生产双官能基烷烃的方法。同时还提供了编码这种酶的核酸和酶，与从碳水化合物饲料中生产双官能基烷烃相关。本发明还提供了重组微生物和代谢途径，用于生产双官能基烷烃。
• Biological Synthesis of Difunctional Hexanes and Pentanes from Carbohydrate Feedstocks
  申请人：Baynes Brain M.

  公开号：US20130017593A1

  公开（公告）日：2013-01-17

  Provided herein are methods for the production of difunctional alkanes in microorganisms. Also provided are enzymes and nucleic acids encoding such enzymes, associated with the difunctional alkane production from carbohydrates feedstocks in microorganisms. The invention also provides recombinant microorganisms and metabolic pathways for the production of difunctional alkanes.

  本文提供了在微生物中生产二官能烷的方法。同时还提供了编码这些酶的酶和核酸，这些酶与从碳水化合物饲料中生产二官能烷有关。本发明还提供了重组微生物和代谢途径，用于生产二官能烷。
• Borrelidin-producing polyketides synthase and its uses
  申请人：Biotica Technology Limited

  公开号：EP1840216A2

  公开（公告）日：2007-10-03

  The present invention relates to the biosynthesis of polyketides and derives from the cloning of nucleic acids encoding a polyketide synthase and other associated proteins involved in the synthesis of the polyketide borrelidin. Materials and methods including enzyme systems, nucleic acids, vectors and cells are provided for the preparation of polyketides including borrelidin and analogues and derivatives thereof. Novel polyketide molecules are also provided.

  本发明与多酮类化合物的生物合成有关，源于对参与合成多酮类化合物硼瑞丁的多酮合成酶和其他相关蛋白的核酸编码的克隆。提供了制备包括硼瑞丁及其类似物和衍生物在内的多酮类化合物的材料和方法，包括酶系统、核酸、载体和细胞。还提供了新型多酮分子。
• Borrelidin-producing polyketide synthase and its uses
  申请人：Biotica Technology Limited

  公开号：EP1961747A2

  公开（公告）日：2008-08-27

  The present invention relates to the biosynthesis of polyketides and derives from the cloning of nucleic acids encoding a polyketide synthase and other associated proteins involved in the synthesis of the polyketide borrelidin. Materials and methods including enzyme systems, nucleic acids, vectors and cells are provided for the preparation of polyketides including borrelidin and analogues and derivatives thereof. Novel polyketide molecules are also provided.

  本发明与多酮类化合物的生物合成有关，源于对参与合成多酮类化合物硼瑞丁的多酮合成酶和其他相关蛋白的核酸编码的克隆。提供了制备包括硼瑞丁及其类似物和衍生物在内的多酮类化合物的材料和方法，包括酶系统、核酸、载体和细胞。还提供了新型多酮分子。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。