(9E,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid | 104832-62-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (9E,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid
• CAS: 104832-62-4
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: JDSRHVWSAMTSSN-WHLLTAFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z,Z)-9,12-十八烷二烯酸二聚物 在 乙二醇双(2-氨基乙基醚)四乙酸 、 lipoxygenase-1 from maize 、 calcium chloride 作用下， 以 aq. buffer 为溶剂， 生成 (9S,10E,12E)-9-hydroperoxyoctadeca-10,12-dienoic acid 、 (9E,11E,13S)-13-Hydroperoxyoctadeca-9,11-dienoic acid 、 (9S,10E,12Z)-9-(氢过氧基)-10,12-十八碳二烯酸 、 13[S-(E,Z)]-hydroperoxy-9,11-octadecadienoic acid
  参考文献：
  名称：

  Calcium modulates membrane association, positional specificity, and product distribution in dual positional specific maize lipoxygenase-1

  摘要：

  This study investigates how calcium modulates the properties of dual positional specific maize lipoxygenase-1, including its interaction with substrate, association with subcellular membrane and alteration of product distribution. Bioinformatic analyses identified Asp(38), Glu(127) and Glu(201) as putative calcium binding residues and Leu(37) as a flanking hydrophobic residue also potentially involved in calcium-mediated binding of the enzyme to subcellular membranes. Asp(38) and Leu(37) were shown to be important but not essential for calcium-mediated association of maize lipoxygenase-1 to subcellular membranes in vitro. Kinetic studies demonstrate that catalytic efficiency (V-max/K-m) shows a bell-shaped dependence on log of the molar ratio of substrate to unbound calcium. Calcium also modulates product distribution of the maize lipoxygenase-1 reaction, favoring 13-positional specificity and increasing the relative amount of (E,Z)-isomeric products. The results suggest that calcium regulates the maize lipoxygenase-1 reaction by binding to substrate, and by promoting binding of substrate to enzyme and association of maize lipoxygenase-1 to subcellular membranes. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.04.001