3-18O-3-hydroxybenzoic acid | 1374456-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-18O-3-hydroxybenzoic acid
• 英文别名: 3-¹⁸O-3-hydroxybenzoic acid
• CAS: 1374456-20-8
• 化学式: C₇H₆O₃
• 分子量: 140.123
• InChiKey: IJFXRHURBJZNAO-PPJXEINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  异分支酸 在 Hyg₅ from Streptomyces hygroscopicus chorismatases 、 isochorismate synthase EntC from E_. coli 、 重氧水 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 2.0h， 生成 3-18O-3-hydroxybenzoic acid
  参考文献：
  名称：

  Chorismatase Mechanisms Reveal Fundamentally Different Types of Reaction in a Single Conserved Protein Fold

  摘要：

  Chorismatases are a class of chorismate-converting enzymes involved in the biosynthetic pathways of different natural products, many of them with interesting pharmaceutical characteristics. So far, three subfamilies of chorismatases are described that convert chorismate into different (dihydro-)benzoate derivatives (CH-FkbO, CH-Hyg5, and CH-XanB2). Until now, the detailed enzyme mechanism and the molecular basis for the different reaction products were unknown. Here we show that the CH-FkbO and CH-Hyg5 subfamilies share the same protein fold, but employ fundamentally different reaction mechanisms. While the FkbO reaction is a typical hydrolysis, the Hyg5 reaction proceeds intramolecularly, most likely via an arene oxide intermediate. Two nonconserved active site residues were identified that are responsible for the different reaction mechanisms in CH-FkbO and CH-Hyg5. Further, we propose an additional amino acid residue to be responsible for the discrimination of the CH-XanB2 subfamily, which catalyzes the formation of two different hydroxybenzoate regioisomers, likely in a single active site. A multiple sequence alignment shows that these three crucial amino acid positions are located in conserved motifs and can therefore be used to assign unknown chorismatases to the corresponding subfamily.

  DOI：

  10.1021/jacs.5b05559

文献信息

• Pathway of Oxygen Incorporation from O2 in TiO2 Photocatalytic Hydroxylation of Aromatics: Oxygen Isotope Labeling Studies
  作者：Yue Li、Bo Wen、Cailan Yu、Chuncheng Chen、Hongwei Ji、Wanhong Ma、Jincai Zhao

  DOI：10.1002/chem.201103446

  日期：2012.2.13

  conditions. The percentage of the products with O2‐derived hydroxyl O atoms increases with the irradiation time, while it decreases with the increase of substrate concentration. More intriguingly, when photogenerated valence‐band holes (hvb+) are removed, nearly all the O atoms (>97 %) in the hydroxyl groups of the hydroxylated products of benzoic acid come from O2, whereas the scavenging of conduction‐band

  羟基化过程是芳族化合物光催化降解的主要步骤，甚至是决定速率的步骤。为了弄清芳烃的羟基化途径，已通过氧同位素标记方法研究了几种模型底物（例如苯甲酸，苯，硝基苯和苄腈）的TiO 2光催化羟基化作用，该方法可以明确地确定芳烃的来源。羟基化产物的羟基中的O原子（来自氧化剂O 2或溶剂H 2 O）。发现羟基化产物的氧源明显取决于反应条件。含O 2的产品百分比衍生的羟基O原子随着辐照时间的增加而增加，而随着底物浓度的增加而减少。更有趣的是，当去除光生价带孔（h vb +）时，苯甲酸羟基化产物的羟基中几乎所有O原子（> 97％）都来自O 2，而导带的清除电子（e CB - ），使几乎所有的羟基氧原子（> 95％）从溶剂ħ起源2 O.在与苯甲酸和苯共存于同一分散体，的O-百分比光催化氧化系统2强吸附的苯甲酸（约30％）的羟基化产物中衍生的羟基O原子比弱吸附的苯（酚）的羟基O原子（> 60％）少得多。这种依