(15S,16R)-epoxy-α-linolenic acid | 138809-17-3

• 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: (15S,16R)-epoxy-α-linolenic acid
• 英文别名: (9Z,12Z)-14-[(2S,3R)-3-ethyloxiran-2-yl]tetradeca-9,12-dienoic acid
• CAS: 138809-17-3
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: HKSDVVJONLXYKL-ADVGRWDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (15S,16R)-epoxy-α-linolenic acid 在 sodium hydroxide 、 高氯酸 、 水 、 氯甲酸乙酯 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  N-(15,16-Dihydroxylinoleoyl)-glutamine and N-(15,16-epoxylinoleoyl)-glutamine isolated from oral secretions of lepidopteran larvae

  摘要：

  N-(15,16-Dihydroxylinoleoyl)-glutamine (1) and N-(15,16-epoxylinoleoyl)-glutamine (2) and were identified in the regurgitant of lepidopteran larvae (Spodoptera exigua and Spodoptera frugiperda) by LC-MS. After methanolysis and derivatisation with MSTFA, the positions of the hydroxy groups of 1 were identified by GC-MS. The structures of both conjugates were confirmed by synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01489-8
• 作为产物：
  描述：

  (9Z,12Z,15Z)-十八碳-9,12,15-三烯过氧酸 以 二氯甲烷 为溶剂， 生成 (15S,16R)-epoxy-α-linolenic acid
  参考文献：
  名称：

  N-(15,16-Dihydroxylinoleoyl)-glutamine and N-(15,16-epoxylinoleoyl)-glutamine isolated from oral secretions of lepidopteran larvae

  摘要：

  N-(15,16-Dihydroxylinoleoyl)-glutamine (1) and N-(15,16-epoxylinoleoyl)-glutamine (2) and were identified in the regurgitant of lepidopteran larvae (Spodoptera exigua and Spodoptera frugiperda) by LC-MS. After methanolysis and derivatisation with MSTFA, the positions of the hydroxy groups of 1 were identified by GC-MS. The structures of both conjugates were confirmed by synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01489-8

文献信息

• Lipoxygenase-catalyzed transformation of epoxy fatty acids to hydroxy-endoperoxides: a potential P450 and lipoxygenase interaction
  作者：Tarvi Teder、William E. Boeglin、Alan R. Brash

  DOI：10.1194/jlr.m054072

  日期：2014.12

  examination of the transformation of the two enantiomers of 15,16-epoxy-α-linolenic acid by soybean LOX-1 revealed that the expected primary product, a 13S-hydroperoxy-15,16-epoxide, underwent a nonenzymatic transformation in buffer into a new derivative that was purified by HPLC and identified by UV, LC-MS, and ¹H-NMR as a 13,15-endoperoxy-16-hydroxy-octadeca-9,11-dienoic acid. The configuration of the endoperoxide

  在此，我们描述了脂氧合酶 (LOX) 对脂肪酸环氧化物的普遍适用转化，该转化导致最终产品中形成五元内过氧化物环。我们在 15,16-环氧-α-亚麻酸代谢中使用大豆 LOX-1 以及在 14,15-环氧二十碳三烯酸代谢中使用鼠血小板型 12-LOX 和人 15-LOX-1 证明了这种转化。 14,15-EET）。对大豆 LOX-1 对 15,16-环氧-α-亚麻酸的两种对映异构体的转化进行的详细检查表明，预期的主要产物 13S-氢过氧-15,16-环氧化物在缓冲液中经历了非酶促转化转化为一种新的衍生物，经 HPLC 纯化，经 UV、LC-MS 和 1H-NMR 鉴定为 13,15-endoperoxy-16-hydroxy-octadeca-9,11-dienoic acid。内过氧化物的构型（顺式或反式侧链）取决于新的氢过氧部分与脂肪酸环氧化物的对映体构型的空间关系。反应机理涉及氢过氧（亲
• Enantioselective epoxidation of linolenic acid catalysed by cytochrome P450BM3 from Bacillus megaterium
  作者：Ayhan Çelik、Davide Sperandio、Robert E. Speight、Nicholas J. Turner

  DOI：10.1039/b506155e

  日期：——

  Cytochrome P450BM3, from Bacillus megaterium, catalyses the epoxidation of linolenic acid 1 yielding 15,16-epoxyoctadeca-9,12-dienoic acid 2 with complete regio- and moderate enantio-selectivity (60% ee). The absolute configuration of the product is tentatively assigned as 15(R),16(S)-. The Michaelis–Menten parameters kcat and Km for the reaction were determined to be 3126 ± 226 min−1 and 24 ± 6 μM respectively.

  来自大肠杆菌的细胞色素P450BM3催化亚油酸1的环氧化反应，生成15,16-环氧油酸2，具有完全的区域选择性和适度的对映选择性（60% ee）。产品的绝对构型暂时被指认为15(R),16(S)-。该反应的米哈利斯-门腾参数kcat和Km分别为3126 ± 226 min−1和24 ± 6 μM。
• Preparation of the enantiomers of hydroxy-C18 fatty acids and their anti-rice blast fungus activities
  作者：Tadahiro Kato、Toshio Nakai、Rumiko Ishikawa、Aya Karasawa、Tsuneo Namai

  DOI：10.1016/s0957-4166(01)00486-4

  日期：2001.10

  the infected rice plants as an enantiomeric mixture with <10% e.e., a procedure for the chemical preparation of both enantiomers was explored, starting from the original fatty acids 4 and 5. The anti-rice blast fungus activities of both enantiomers of the allylic alcohols 1–3 and epoxy α-linolenic acids 12 and 13 demonstrate no noticeable correlation between the activity and chirality.

  为了检查抗稻瘟病菌的活性和烯丙基醇的手性之间的相关性1 - 3，这是从受感染的水稻植物，其特征为具有<10％ee的，对于两者的化学制备过程对映体混合物从原始脂肪酸4和5开始探索对映体。烯丙基醇的两种对映体的抗稻瘟病菌的活动13和环氧树脂α-亚麻酸12和13表现出的活性和手性之间没有明显的相关性。
• Oxidation of C18 Hydroxy-Polyunsaturated Fatty Acids to Epoxide or Ketone by Catalase-Related Hemoproteins Activated with Iodosylbenzene
  作者：Tarvi Teder、William E. Boeglin、Alan R. Brash

  DOI：10.1007/s11745-017-4271-0

  日期：2017.7

  and 9,10‐epoxy‐13‐keto derivatives; equivalent transformations occurred with 9S‐hydroxy‐linoleic acid as substrate. In parallel incubations in the presence of iodosylbenzene, human catalase displayed no activity towards 13S‐hydroxy‐linoleic acid, as expected from the highly restricted access to its active site. The results indicated that with suitable transformation to Compound I, monooxygenase activity

  当使用碘基苯激活时，检查了与过氧化氢酶相关的小型过氧化氢酶相关的血蛋白，它们可以与脂肪酸氢过氧化物反应，以检测其潜在的单加氧酶活性。测试的蛋白为镰刀镰刀菌41 kD过氧化氢酶血红蛋白（Fg-cat，基因FGSG_02217），荧光假单胞菌Pfl01过氧化氢酶（37.5 kD，保藏号WP_011333788.1）和鸟分枝杆菌ssp。副结核病33 kD过氧化氢酶（基因MAP-2744c）。选择13-羟基-十八碳烯酸（通常不反应）作为底物，因为这些酶会与相应的13 S-氢过氧化物特异性反应（Pakhomova等人18：2559-2568，5; Teder等人。1862：706–715，14）。在亚碘酰苯FG-猫的存在下转化13 š羟基脂肪酸两种产品：13 15,16-双键š羟基α亚麻酸被立体特异性地氧化为15小号，16 - [R -顺-epoxide或13-羟基被氧化为13-酮。通过UV，HPL
• Highly Terminal-Selective Epoxidation of Linolenic Acid with an Amphiphilic Iron Porphyrin Catalyst Casted in Bilayer Membranes
  作者：Yoshinori Naruta、Masa-oki Goto、Toshifumi Tawara、Fumito Tani

  DOI：10.1246/cl.2002.162

  日期：2002.2

  An amphiphilic iron porphyrin having four hexadecanoic acid chains on each face of the porphyrin was prepared and the catalytic epoxidation of linolenic acid with the heme-casted bilayer membranes was achieved in high regioselectivity at the terminal double bond of the substrate. The orientation of the porphyrin ring in the membrane was determined to be parallel to the aqueous-bilayer interface by means of ESR.

  制备了一种两亲性铁卟啉，卟啉的每个面上都有四条十六烷酸链，用这种血红素浇铸的双层膜催化亚麻酸的环氧化反应，在底物的末端双键处实现了高区域选择性。通过 ESR，确定了膜中卟啉环的取向与水层界面平行。