5(R)-羟化二十烷四烯酸 | 61641-47-2

• 物质功能分类: 生物化工 - 生化试剂
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 5(R)-羟化二十烷四烯酸
• 英文名称: (5R)-HETE
• 英文别名: 5R-hydroxy-6E,8Z,11Z,14Z-eicosatetraenoic acid；(5R,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
• CAS: 61641-47-2
• 化学式: C₂₀H₃₂O₃
• 分子量: 320.472
• InChiKey: KGIJOOYOSFUGPC-CABOLEKPSA-N

物化性质

• 沸点：
  487.7±45.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)
• 溶解度：
  0.1 M Na2CO3：2 mg/mL； DMF：可混溶； DMSO：可混溶；乙醇：可混溶； PBS pH 7.2：0.8 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090

反应信息

• 作为反应物：
  描述：

  5(R)-羟化二十烷四烯酸 在 吡啶 作用下， 以 乙醚 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 18.0h， 生成
  参考文献：
  名称：

  5-脂加氧酶和环加氧酶-2 的生物合成交叉产生 5-羟基-PGE2 和 5-羟基-PGD2

  摘要：

  5-脂氧合酶 (5-LOX) 和环氧合酶-2 (COX-2) 酶活性的生物合成交叉是将花生四烯酸转化为独特的类二十烷酸的有效途径。在这里，我们表明 COX-2 催化 5-LOX 衍生的 5-羟基-二十碳四烯酸产生内过氧化物 5-羟基-PGH 2 ，它自发重排为 5-OH-PGE 2和 5-OH-PGD 2 ，即 5-OH-PGD 2 。花生四烯酸衍生的PGE 2和PGD 2的羟基类似物。内过氧化物通过其预测的降解产物5,12-二羟基-十七-6 E ,8 E ,10 E -烯酸以及SnCl 2介导的5-OH-PGF 2α还原来鉴定。 5-OH-PGE 2和5-OH-PGD 2均不稳定并且在弱碱处理后迅速降解。这种不稳定性阻碍了生物样品中的检测，通过使用 NaBH 4原位还原产生相应的稳定 5-OH-PGF 2非对映异构体克服了这种不稳定性，并能够在活化的原代人白细胞中检测 5-OH-PGF 2α

  DOI：

  10.1021/jacsau.1c00177
• 作为产物：
  描述：

  (Z,Z)-1-iodo-3,6-dodecadiene 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 水 、 甲苯 为溶剂， 生成 5(R)-羟化二十烷四烯酸
  参考文献：
  名称：

  Stereospecific synthesis of 5S-HETE, 5R-HETE and their transformation to 5(±)HPETE

  摘要：

  DOI：

  10.1016/s0040-4039(00)81586-5

文献信息

• Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways
  作者：Aldwin Anterola、Cornelia Göbel、Ellen Hornung、George Sellhorn、Ivo Feussner、Howard Grimes

  DOI：10.1016/j.phytochem.2008.11.012

  日期：2009.1

  Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 alpha-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering plants. To identify the fatty acid substrates used by moss lipoxygenases, eight lipoxygenase genes from Physcomitrella patens were heterologously expressed in Escherichia coli, and then analyzed for lipoxygenase activity using linoleic, alpha-linolenic and arachidonic acids as substrates. Among the eight moss lipoxygenases, only seven were found to be enzymatically active in vitro, two of which selectively used arachidonic acid as the substrate, while the other five preferred alpha-linolenic acid. Based on enzyme assays using a Clark-type oxygen electrode, all of the active lipoxygenases had an optimum pH at 7.0, except for one with highest activity at pH 5.0. HPLC analyses indicated that the two arachidonic acid lipoxygenases form (12S)-hydroperoxy eicosatetraenoic acid as the main product, while the other five lipoxygenases produce mainly (13S)-hydroperoxy octadecatrienoic acid from alpha-linolenic acid. These results suggest that mosses may have both C20 and C18 based oxylipin pathways. Published by Elsevier Ltd.
• Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2
  作者：Surafel Mulugeta、Takashi Suzuki、Noemi Tejera Hernandez、Markus Griesser、William E. Boeglin、Claus Schneider

  DOI：10.1194/jlr.m001719

  日期：2010.3

  Biosynthesis of the prostaglandin endoperoxide by the cyclooxygenase (COX) enzymes is accompanied by formation of a small amount of 11R-hydroxyeicosatetraenoic acid (HETE), 15R-HETE, and 15S-HETE as by-products. Acetylation of COX-2 by aspirin abrogates prostaglandin synthesis and triggers formation of 15R-HETE as the sole product of oxygenation of arachidonic acid. Here, we investigated the formation of by-products of the transformation of 5S-HETE by native COX-2 and by aspirin-acetylated COX-2 using HPLC-ultraviolet, GC-MS, and LC-MS analysis. 5S,15S- dihydroxy (di)HETE, 5S,15R-diHETE, and 5S,11R-diHETE were identified as by-products of native COX-2, in addition to the previously described di-endoperoxide (5S,15S-dihydroxy-9S,11R,8S,12S-diperoxy-6E,13E-eicosadienoic acid) as the major oxygenation product. 5S,15R-diHETE was the only product formed by aspirin-acetylated COX-2. Both 5,15-diHETE and 5,11-diHETE were detected in CT26 mouse colon carcinoma cells as well as in lipopolysaccharide-activated RAW264.7 cells incubated with 5S-HETE, and their formation was attenuated in the presence of the COX-2 specific inhibitor, NS-398. Aspirin-treated CT26 cells gave 5,15-diHETE as the most prominent product formed from 5S-HETE. 5S,15S-diHETE has been described as a product of the cross-over of 5-lipoxygenase (5-LOX) and 15-LOX activities in elicited rat mononuclear cells and human leukocytes, and our studies implicate crossover of the 5-LOX and COX-2 pathways as an additional bio-synthetic route.-Mulugeta, S., T. Suzuki, N. T. Hernandez, M. Griesser, W. E. Boeglin, and C. Schneider. Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5S-HETE by native and aspirin-acetylated COX-2. J. Lipid Res. 2010. 51: 575-585.
• Stereospecific synthesis of 5S-HETE, 5R-HETE and their transformation to 5(±)HPETE
  作者：Robert Zamboni、Joshua Rokach

  DOI：10.1016/s0040-4039(00)81586-5

  日期：1983.1
• Biosynthetic Crossover of 5-Lipoxygenase and Cyclooxygenase-2 Yields 5-Hydroxy-PGE₂ and 5-Hydroxy-PGD₂
  作者：Fumie Nakashima、Takashi Suzuki、Odaine N. Gordon、Dominic Golding、Toshiaki Okuno、Juan A. Giménez-Bastida、Takehiko Yokomizo、Claus Schneider

  DOI：10.1021/jacsau.1c00177

  日期：2021.9.27

  (COX-2) enzymatic activities is a productive pathway to convert arachidonic acid into unique eicosanoids. Here, we show that COX-2 catalysis with 5-LOX derived 5-hydroxy-eicosatetraenoic acid yields the endoperoxide 5-hydroxy-PGH2 that spontaneously rearranges to 5-OH-PGE2 and 5-OH-PGD2, the 5-hydroxy analogs of arachidonic acid derived PGE2 and PGD2. The endoperoxide was identified via its predicted

  5-脂氧合酶 (5-LOX) 和环氧合酶-2 (COX-2) 酶活性的生物合成交叉是将花生四烯酸转化为独特的类二十烷酸的有效途径。在这里，我们表明 COX-2 催化 5-LOX 衍生的 5-羟基-二十碳四烯酸产生内过氧化物 5-羟基-PGH 2 ，它自发重排为 5-OH-PGE 2和 5-OH-PGD 2 ，即 5-OH-PGD 2 。花生四烯酸衍生的PGE 2和PGD 2的羟基类似物。内过氧化物通过其预测的降解产物5,12-二羟基-十七-6 E ,8 E ,10 E -烯酸以及SnCl 2介导的5-OH-PGF 2α还原来鉴定。 5-OH-PGE 2和5-OH-PGD 2均不稳定并且在弱碱处理后迅速降解。这种不稳定性阻碍了生物样品中的检测，通过使用 NaBH 4原位还原产生相应的稳定 5-OH-PGF 2非对映异构体克服了这种不稳定性，并能够在活化的原代人白细胞中检测 5-OH-PGF 2α