2-(3,4-dioxocyclohexa-1,5-dien-1-yl)acetic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3,4-dioxocyclohexa-1,5-dien-1-yl)acetic acid
• 化学式: C₈H₆O₄
• 分子量: 166.133
• InChiKey: GACPQMGBTJGBAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,4-dioxocyclohexa-1,5-dien-1-yl)acetic acid 生成 3,4-二羟基苯乙酸
  参考文献：
  名称：

  Enzymically Amplified Voltammetric Sensor for Microliter Sample Volumes of Salicylate

  摘要：

  A new voltammetric sensing strategy for salicylate employing two enzymes and applicable to microliter sample volumes is demonstrated, The method involves the use of the enzyme salicylate hydroxylase to convert salicylate to catechol, which is oxidized at a carbon electrode, The product of this oxidation reaction, o-quinone, is then reduced by a second enzyme, glucose oxidase, to regenerate catechol, Reoxidation of catechol results in a signal that is amplified due to repeated cycling of catechol molecules between the oxidized and reduced states, This chemistry is implemented in two configurations, (i) A paper disk into which both enzymes have been absorbed is mounted on a coplanar three electrode assembly for aqueous experiments, Determination of salicylate in a nonprescription dermatological product is demonstrated, (ii) A small solution volume confined directly on the coplanar electrodes is used for determination of salicylate in whole blood, The advantages of the use of two enzymes and of monitoring steady-state catalytic currents are discussed.

  DOI：

  10.1021/ac00107a022
• 作为产物：
  描述：

  3,4-二羟基苯乙酸 在 酪氨酸酶 作用下， 以 aq. buffer 为溶剂， 反应 0.07h， 生成 2-(3,4-dioxocyclohexa-1,5-dien-1-yl)acetic acid
  参考文献：
  名称：

  同原儿茶酸 2,3-双加氧酶的底物介导的氧活化：由酪氨酸 257 变体形成的中间体

  摘要：

  高原儿茶酸（HPCA；3,4-二羟基苯乙酸酯或 4-羧甲基儿茶酚）和 O 2在高原儿茶酸 2,3-双加氧酶 (FeHPCD)的活性位点 Fe II的相邻配体位点结合。我们提出电子从螯合的芳香底物通过 Fe II转移到 O 2赋予两种底物自由基特性。这将促进底物之间的反应以形成烷基过氧中间体，作为芳环裂解的第一步。一些活性位点氨基酸被认为通过酸/碱化学、氢键和静电相互作用促进这些反应。这里使用 Tyr257Phe (Y257F) 变体探索了 Tyr257 的作用，该变体降低了k cat约 75%。FeHPCD-HPCA 复合物的晶体结构表明，Tyr257 与 HPCA 的去质子化的 C2-羟基形成氢键。停流研究表明，至少两种反应中间体，称为 Y257F Int1 HPCA和 Y257F Int2 HPCA，在形成开环产物之前的 Y257F-HPCA + O 2反应过程中积累。Y257F Int1

  DOI：

  10.1021/bi301114x

文献信息

• The Metabolic Fate of ortho-Quinones Derived from Catecholamine Metabolites
  作者：Shosuke Ito、Yuta Yamanaka、Makoto Ojika、Kazumasa Wakamatsu

  DOI：10.3390/ijms17020164

  日期：——

  ortho-quinones and the identification of their reaction products. Spectrophotometric examination showed that the ortho-quinones initially formed underwent extensive degradation at pH 6.8. HPLC analysis showed that DOPE-quinone and DOPEG-quinone degraded with half-lives of 15 and 30 min at pH 6.8, respectively, and >100 min at pH 5.3. The major product from DOPE-quinone was DOPEG which was produced through

  邻奎宁酮是通过酶（例如酪氨酸酶）或过渡金属离子氧化邻苯二酚底物而在体内产生的。神经黑素是存在于大脑黑质和大脑蓝斑中的一种深色色素，是通过多巴胺（DA）和去甲肾上腺素（NE）与半胱氨酸的相互作用而产生的，但它也掺入了它们的酒精和酸性代谢产物。在这项研究中，我们研究了儿茶酚胺代谢物，3,4-二羟基苯基乙醇（DOPE），3,4-二羟基苯基乙二醇（DOPEG），3,4-二羟基苯基乙酸（DOPAC）和3,4衍生的邻醌的代谢命运。 -二羟基苯基扁桃酸（DOMA）。蘑菇酪氨酸酶氧化邻苯二酚底物，然后进行紫外可见分光光度法。用NaBH 3或抗坏血酸还原后进行HPLC分析，可以测量邻醌的半衰期并鉴定其反应产物。分光光度检查表明，最初形成的邻醌在pH 6.8时发生了广泛的降解。HPLC分析表明，DOPE-醌和DOPEG-醌在pH 6.8下分别以15和30分钟的半衰期降解，在pH 5.3下> 100分钟的半衰期
• Determination and Applications of the Molar Absorptivity of Phenolic Adducts with Captopril and Mesna
  作者：F. García-Molina、J. L. Muñoz-Muñoz、M. García-Molina、M. Molina-Alarcon、P. A. García-Ruíz、J. Tudela、J. N. Rodríguez-López

  DOI：10.1021/jf803447g

  日期：2009.2.25

  Captopril and mesna are molecules with a free thiol group, used as active ingredients due to their hypotensor and mucolytic properties, respectively. These compounds cross the hematoencephalic barrier and, due to the reactivity of their thiol group, can form adducts with the o-quinones formed during the oxidation of mono- and o-diphenols. Polyphenol oxidase from plants and fungi can be used as a tool for generating o-quinones in their action on o-diphenols and facilitate the formation of adducts in the presence of captopril or mesna. The spectrophotometric characterization of these adducts is useful from several points of view. Here, using the end-point method, which involves the exhaustion of oxygen in the medium, we determined the molar absorptivity of the adducts of different o-diphenols with captopril and mesna. Besides the analytical interest of this approach, we also use it to make a kinetic characterization of polyphenol oxidase as it acts on o-diphenolic substrates that produce unstable o-quinones.
• JEON, HEE-KYOUNG;NOHTA, HITOSHI;OHKURA, YOSUKE, ANAL. SCI., 6,(1990) N, C. 677-682
  作者：JEON, HEE-KYOUNG、NOHTA, HITOSHI、OHKURA, YOSUKE

  DOI：——

  日期：——
• JEON, HEE-KYOUNG;NOHTA, HITOSHI;NAGAOKA, HIROAKI;OHKURA, YOSUKE, ANAL. SCI., 7,(1991) N, C. 257-262
  作者：JEON, HEE-KYOUNG、NOHTA, HITOSHI、NAGAOKA, HIROAKI、OHKURA, YOSUKE

  DOI：——

  日期：——