(13R,9Z,11E)-13-hydroperoxy-9,11-octadecadienoic acid | 73036-16-5

• 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: (13R,9Z,11E)-13-hydroperoxy-9,11-octadecadienoic acid
• 英文别名: 13-(R)-hydroperoxyoctadecadienoic acid；(9Z,11E,13R)-13-hydroperoxyoctadeca-9,11-dienoic acid
• CAS: 73036-16-5
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: JDSRHVWSAMTSSN-PIHGWCCBSA-N

物化性质

• 沸点：
  449.9±28.0 °C(Predicted)
• 密度：
  1.002±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  (13R,9Z,11E)-13-hydroperoxy-9,11-octadecadienoic acid 在 fatty acid hydroperoxide lyase from Nicotiana tabacum 、 Na-Pi buffer 作用下， 生成 正己醛
  参考文献：
  名称：

  体外培养的烟草细胞中的脂肪酸氢过氧化物裂解酶

  摘要：

  摘要 在体外培养的绿色和非绿色烟草细胞中发现了脂肪酸氢过氧化物裂解酶（HPO裂解酶）。非绿色细胞中的 HPO 裂解酶活性是绿色细胞中的 1 3 - 1 2 。当细胞从亮处转移到暗处或反之时，细胞根据光照条件变为非绿色或绿色。HPO裂解酶活性也随光照条件而变化，但HPO裂解酶活性的变化与叶绿素含量的变化不成正比。这些结果表明绿色细胞中至少存在两种​​类型的 HPO 裂解酶。一种类型的 HPO 裂解酶可能对绿色和非绿色细胞都很常见；另一种是叶绿体。细胞的脂肪酸组成和 HPO 裂解酶的底物特异性在绿色和非绿色细胞之间不同。

  DOI：

  10.1016/s0031-9422(00)84072-8
• 作为产物：
  描述：

  甘油三亚油酸酯 在 borate buffer 、 氧气 作用下， 以 正辛烷 为溶剂， 反应 5.0h， 生成 (13R,9Z,11E)-13-hydroperoxy-9,11-octadecadienoic acid
  参考文献：
  名称：

  从三油精化学酶法生产（+）-胆酸：耦合合成和萃取

  摘要：

  AbstractChemoenzymatic conversion of trilinolein to (+)‐coriolic acid was investigated in this work. Lipase‐catalyzed hydrolysis of trilinolein and lipoxygenation of liberated linoleic acid were coupled in a two‐phase medium that consisted of a pH 9 borate buffer and a water‐immiscible organic solvent (octane). High concentrations of trilinolein could be dissolved in the organic phase (up to 340 mM). Linoleic acid, liberated after hydrolysis, transferred to the aqueous phase and was enzymatically converted to the preferred 13(S)‐hydroperoxy‐9Z,11E‐octadecadienoic acid with soybean lipoxygenase‐1. This product, which remained in the aqueous phase, could be recovered by centrifugation and then chemically reduced to (+)‐coriolic acid (purity >95%). Recovery of this compound by liquid‐liquid extraction was easy. The structure of (+)‐coriolic acid has been confirmed by 1H nuclear magnetic resonance spectroscopy, mass spectrometry, and infrared spectroscopy. High yields were obtained with pure trilinolein or sunflower oil as initial substrates.

  DOI：

  10.1007/s11746-997-0196-8

文献信息

• Identification of an amino acid determinant of pH regiospecificity in a seed lipoxygenase from Momordica charantia
  作者：Ellen Hornung、Susan Kunze、Alena Liavonchanka、Grit Zimmermann、Diana Kühn、Kathrin Fritsche、Andreas Renz、Hartmut Kühn、Ivo Feussner

  DOI：10.1016/j.phytochem.2008.09.006

  日期：2008.11

  Lipoxygenases (LOX) form a heterogeneous family of lipid peroxidizing enzymes, which catalyze specific dioxygenation of polyunsaturated fatty acids. According to their positional specificity of linoleic acid oxygenation plant LOX have been classified into linoleate 9- and linoleate 13-LOX and recent reports identified a critical valine at the active site of 9-LOX. In contrast, more bulky phenylalanine or histidine residues were found at this position in 13-LOX. We have recently cloned a LOX-isoform from Momordica charantia and multiple amino acid alignments indicated the existence of a glutamine (Gln599) at the position were 13-LOX usually carry histidine or phenylalanine residues. Analyzing the pH-dependence of the positional specificity of linoleic acid oxygenation we observed that at pH-values higher than 7.5 this enzyme constitutes a linoleate 13-LOX whereas at lower pH, 9-H(P)ODE was the major reaction product. Site-directed mutagenesis of glutamine 599 to histidine (Gln599His) converted the enzyme to a pure 13-LOX. These data confirm previous observation suggesting that reaction specificity of certain LOX-isoforms is not an absolute enzyme property but may be impacted by reaction conditions such as pH of the reaction mixture. We extended this concept by identifying glutamine 599 as sequence determinant for such pH-dependence of the reaction specificity. Although the biological relevance for this alteration switch remains to be investigated it is of particular interest that it occurs at near physiological conditions in the pH-range between 7 and 8. (C) 2008 Elsevier Ltd. All rights reserved.
• Production of 13(S)-hydroperoxy-9(Z),11(E)-octadecadienoic acid using soybean lipoxygenase 1 in a biphasic octane-water system
  作者：Philippe Drouet、Daniel Thomas、Marie Dominique Legoy

  DOI：10.1016/s0040-4039(00)76703-7

  日期：1994.6

  The synthetic potential of soybean lipoxygenase 1 (LOX 1) for the synthesis of 13(S) hydroperoxy-9(Z),11(E)-octadecadienoic acid is investigated in a biphasic medium (octane; berate buffer, pH 9.6) Improvement of the reaction yield (compared to an aqueous system) is observed at very high concentrations (20-40 g/L). The regioselectivity of the reaction is not affected by the presence of the organic phase.
• Steric Control of Oxygenation Regiochemistry in Soybean Lipoxygenase-1
  作者：Michael J. Knapp、Florian P. Seebeck、Judith P. Klinman

  DOI：10.1021/ja003855k

  日期：2001.3.1
• Grechkin; Hamberg, Russian Journal of Bioorganic Chemistry, 1996, vol. 22, # 12, p. 827 - 828
  作者：Grechkin、Hamberg

  DOI：——

  日期：——
• Fatty acid hydroperoxide lyase in tobacco cells cultured in vitro
  作者：Jiro Sekiya、Satoru Tanigawa、Tadahiko Kajiwara、Akikazu Hatanaka

  DOI：10.1016/s0031-9422(00)84072-8

  日期：1984.1

  Abstract Fatty acid hydroperoxide lyase (HPO lyase) was found in green and non-green tobacco cells cultured in vitro . The HPO lyase activity in non-green cells was 1 3 - 1 2 of that in green cells. When the cells were transferred from the light to dark conditions or vice versa , cells turned non-green or green according to the light conditions. The HPO lyase activity also changed according to the

  摘要 在体外培养的绿色和非绿色烟草细胞中发现了脂肪酸氢过氧化物裂解酶（HPO裂解酶）。非绿色细胞中的 HPO 裂解酶活性是绿色细胞中的 1 3 - 1 2 。当细胞从亮处转移到暗处或反之时，细胞根据光照条件变为非绿色或绿色。HPO裂解酶活性也随光照条件而变化，但HPO裂解酶活性的变化与叶绿素含量的变化不成正比。这些结果表明绿色细胞中至少存在两种​​类型的 HPO 裂解酶。一种类型的 HPO 裂解酶可能对绿色和非绿色细胞都很常见；另一种是叶绿体。细胞的脂肪酸组成和 HPO 裂解酶的底物特异性在绿色和非绿色细胞之间不同。