(1Z,3Z)-2-carboxy-muconic acid | 1116-26-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1Z,3Z)-2-carboxy-muconic acid
• 英文别名: 3-carboxy-cis,cis-muconic acid；buta-1,3-diene-1c,2,4c-tricarboxylic acid；Buta-1,3-dien-1c,2,4c-tricarbonsaeure；Β-Carboxy-cis-cis-muconsaeure；β-Carboxy-cis.cis-muconsaeure；β-Carboxy-cis,cis-muconat；(1E,3Z)-buta-1,3-diene-1,2,4-tricarboxylic acid
• CAS: 1116-26-3
• 化学式: C₇H₆O₆
• 分子量: 186.121
• InChiKey: KJOVGYUGXHIVAY-BXTBVDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1Z,3Z)-2-carboxy-muconic acid 在 盐酸 作用下， 生成 buta-1,3-diene-1c,2,4t-tricarboxylic acid
  参考文献：
  名称：

  β-羧基和β-羟甲基-粘康衍生物的立体化学

  摘要：

  Nmr光谱已用于确定各种β-羧基和β-羟甲基粘康酸衍生物的立体化学。讨论了烯烃质子之间的远距离自旋耦合。的αβ-和异构化γ δ-双键已被证明分别涉及δ-和α羧基基团的参与。两个β羧基的治疗顺-顺-和顺式-反式-muconic酸与热的含水碱得到，相反与先前的报告中，反式-glutaconic酸而不是β羧基-反式-反式-muconic酸。描述了一种方便的制备δ-氘代的β-羧基粘康糖衍生物的方法。

  DOI：

  10.1039/j39680001483
• 作为产物：
  描述：

  原儿茶酸 在 protecatechuate 3,4-dioxygenase 、 水 、 氧气 作用下， 生成 (1Z,3Z)-2-carboxy-muconic acid
  参考文献：
  名称：

  在活化的多孔玻璃珠上固定平菇原儿茶酸 3,4-双加氧酶

  摘要：

  摘要 从木材降解真菌 Pleurotus ostreatus 中纯化的原儿茶酸 3,4-双加氧酶（原儿茶酸：氧 3,4-氧化还原酶，EC 1.13.11.3）固定在玻璃珠上。附着的蛋白质百分比为 78，保留的酶活性为 90%。测试了固定化酶的基本特性，并与可溶性形式的酶进行了比较。固定化双加氧酶在很宽的 pH 值和温度范围内都是稳定的。此外，固定导致其比活性略有增加。

  DOI：

  10.1016/0031-9422(88)80651-4

文献信息

• STUDIES IN THE POLYOXYPHENOL SERIES: VII. THE OXIDATION OF VANILLIN WITH SODIUM CHLORITE AND CHLORINE DIOXIDE
  作者：R. M. Husband、C. D. Logan、C. B. Purves

  DOI：10.1139/v55-010

  日期：1955.1.1

  Vanillin almost instantly reduced 1.2 to 1.5 moles of aqueous chlorine dioxide at 20 °C. or 5 °C. and any pH between 1.2 and 6.5, and a white crystalline substance with the composition of a dihydroxyvanillin, C₇H₅O₄(OCH₃), was isolated in roughly 25% yield independently of the pH. When oxidized with aqueous sodium chlorite at 20 °C. and pH 0.5, these crystals gave another crystalline substance with the composition of a dihydroxyvanillic acid, C₇H₅O₅(OCH₃). Although both these substances decomposed readily to red oils and then to brown powders free of methoxyl groups, seven well characterized derivatives were prepared. The results showed that the substances were unsaturated, monohydroxy, diketone tautomers of a dihydroxyvanillin and the corresponding dihydroxyvanillic acid, but precise structures could not be assigned. Parallel oxidations of vanillin with aqueous sodium chlorite at 20 °C. and pH 6 proceeded at a negligible rate, but near pH 5 a reaction that often seemed autocatalytic produced about 19% of 5-chlorovanillin. At pH 4 the aldehyde C₇H₅O₄(OCH₃) was isolated in 19% yield; at pH 1 this aldehyde (15%) was mixed with 7.7% of the corresponding acid C₇H₅O₅(OCH₃), but at pH 0.5 the latter alone was produced (28%). Chlorine dioxide and sodium chlorite therefore differed markedly in their oxidizing action and in the effect of pH upon it. When acting on vanillin, both oxidants also produced deep red, unstable oils with quinone-like properties and often containing chlorine.

  香草醛在20°C或5°C的任何pH值下，几乎立即将1.2至1.5摩尔的水溶氯氧化物还原，得到一种白色结晶物质，其组成为双羟基香草醛，C7H5O4(OCH3)，收率约为25％，与pH无关。当在20°C和pH 0.5下用水溶氯酸钠氧化这些晶体时，得到另一种双羟基香草酸的结晶物质，C7H5O5(OCH3)。虽然这两种物质很容易分解为不含甲氧基的红色油和褐色粉末，但已制备出七种经充分表征的衍生物。结果表明，这些物质是双羟基香草醛和相应的双羟基香草酸的不饱和、单羟基、二酮互变异构体，但精确的结构无法确定。在20°C和pH 6下，香草醛与水溶氯酸钠的平行氧化反应几乎不发生，但在接近pH 5时，常常出现一种看似自催化的反应，产生约19％的5-氯香草醛。在pH 4时，醛C7H5O4(OCH3)的收率为19％；在pH 1时，这种醛（15％）与相应的酸C7H5O5(OCH3)（7.7％）混合，但在pH 0.5时仅产生后者（28％）。因此，氯气和氯酸钠在氧化作用和pH影响上有明显的差异。在作用于香草醛时，这两种氧化剂也会产生深红色、不稳定的类醌油，通常含氯。
• <i>In vitro</i> reconstitution of the catabolic reactions catalyzed by PcaHG, PcaB, and PcaL: the protocatechuate branch of the β-ketoadipate pathway in <i>Rhodococcus jostii</i> RHA1
  作者：Tomoya Yamanashi、Seung-Young Kim、Hirofumi Hara、Nobutaka Funa

  DOI：10.1080/09168451.2014.993915

  日期：2015.5.4

  The β-ketoadipate pathway is a major pathway involved in the catabolism of the aromatic compounds in microbes. The recent progress in genome sequencing has led to a rapid accumulation of genes from the β-ketoadipate pathway in the available genetic database, yet the functions of these genes remain uncharacterized. In this study, the protocatechuate branch of the β-ketoadipate pathway of Rhodococcus

  β-酮己二酸途径是微生物中芳香族化合物分解代谢的主要途径。基因组测序的最新进展已导致可利用的遗传数据库中来自β-酮己二酸途径的基因迅速积累，但这些基因的功能仍未表征。在这项研究中，何氏红球菌的β-酮己二酸途径的原儿茶酸分支在体外被重建。通过高效液相色谱法分析了PcaHG，PcaB和PcaL的反应产物。使用LC-MS和核磁共振进一步表征了这些反应产物β-酮己二酸酯烯醇-内酯，3-羧基-顺式，顺式-粘康酸酯，γ-羧基粘康内酯，粘康内酯和β-酮己二酸酯。此外，PcaL的体外反应 首次证明了由γ-羧基-粘康内酯脱羧酶和β-酮己二酸酯烯醇-内酯水解酶活性组成的双结构域蛋白。这项工作为分析与遗传数据库中沉积的β-酮己二酸途径增加有关的酶的催化特性提供了基础。
• Sequence-determined DNA fragments and corresponding polypeptides encoded thereby
  申请人：Ceres Incorporated

  公开号：EP1033405A2

  公开（公告）日：2000-09-06

  The present invention provides DNA molecules that constitute fragments of the genome of a plant, and polypeptides encoded thereby. The DNA molecules are useful for specifying a gene product in cells, either as a promoter or as a protein coding sequence or as an UTR or as a 3' termination sequence, and are also useful in controlling the behavior of a gene in the chromosome, in controlling the expression of a gene or as tools for genetic mapping, recognizing or isolating identical or related DNA fragments, or identification of a particular individual organism, or for clustering of a group of organisms with a common trait. 0Arabidopsis DNA is used in the present experiment, but the procedure is a general one.

  本发明提供了构成植物基因组片段的 DNA 分子及其编码的多肽。这些 DNA 分子可作为启动子或蛋白质编码序列或 UTR 或 3'终止序列，用于指定细胞中的基因产物，也可用于控制染色体中基因的行为，控制基因的表达，或作为基因绘图、识别或分离相同或相关 DNA 片段、或识别特定生物个体、或对具有共同性状的生物群体进行聚类的工具。 本实验中使用的是拟南芥 DNA，但这是一个通用程序。
• DNA Sequences
  申请人：Ceres Incorporated

  公开号：EP1887081A2

  公开（公告）日：2008-02-13

  The present invention provides DNA molecules that constitute fragments of the genome of a plant, and polypeptides encoded thereby. The DNA molecules are useful for specifying a gene product in cells, either as a promoter or as a protein coding sequence or as an UTR or as a 3' termination sequence, and are also useful in controlling the behavior of a gene in the chromosome, in controlling the expression of a gene or as tools for genetic mapping, recognizing or isolating identical or related DNA fragments, or identification of a particular individual organism, or for clustering of a group of organisms with a common trait.

  本发明提供了构成植物基因组片段的 DNA 分子及其编码的多肽。这些 DNA 分子可作为启动子或蛋白质编码序列或 UTR 或 3'终止序列，用于指定细胞中的基因产物，也可用于控制染色体中基因的行为，控制基因的表达，或作为基因绘图、识别或分离相同或相关 DNA 片段、或识别特定生物个体或具有共同性状的生物群体的工具。
• 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。