9S,10S-trans-epoxy-11S-threo-hydroxy-octadec-12Z-enoic acid | 906531-52-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 9S,10S-trans-epoxy-11S-threo-hydroxy-octadec-12Z-enoic acid
• 英文别名: (9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid；8-[(2S,3S)-3-[(Z,1S)-1-hydroxyoct-2-enyl]oxiran-2-yl]octanoic acid
• CAS: 906531-52-0
• 化学式: C₁₈H₃₂O₄
• 分子量: 312.45
• InChiKey: RQBBZCMCNSJACV-MLYFJTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  22.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.06
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 9S,10S-trans-epoxy-11S-threo-hydroxy-octadec-12Z-enoic acid 以 乙醚 为溶剂， 生成 、
  参考文献：
  名称：

  Epoxyalcohol synthase of Ectocarpus siliculosus . First CYP74-related enzyme of oxylipin biosynthesis in brown algae

  摘要：

  Enzymes of CYP74 family play the central role in the biosynthesis of physiologically important oxylipins in land plants. Although a broad diversity of oxylipins is known in the algae, no CYP74s or related enzymes have been detected in brown algae yet. Cloning of the first CYP74-related gene CYP5164B1 of brown alga Ectocarpus siliculosus is reported in present work. The recombinant protein was incubated with several fatty acid hydroperoxides. Linoleic acid 9-hydroperoxide (9-HPOD) was the preferred substrate, while linoleate 13-hydroperoxide (13-HPOD) was less efficient. a.-Linolenic acid 9- and 13-hydroperoxides, as well as eicosapentaenoic acid 15-hydroperoxide were inefficient substrates. Both 9-HPOD and 13-HPOD were converted into epoxyalcohols. For instance, 9-HPOD was turned primarily into (9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid. Both epoxide and hydroxyl oxygen atoms of the epoxyalcohol were incorporated mostly from [O-18(2)]9-HPOD. Thus, the enzyme exhibits the activity of epoxyalcohol synthase (EsEAS). The results show that the EsEAS isomerizes the hydroperoxides into epoxyalcohols via epoxyallylic radical, a common intermediate of different CYP74s and related enzymes. EsEAS can be considered as an archaic prototype of CYP74 family enzymes. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbalip.2016.11.007
• 作为产物：
  描述：

  (9S,10E,12Z)-9-(氢过氧基)-10,12-十八碳二烯酸 在 recombinant Ectocarpus siliculosus CYP₅₁₆₄B₁ enzyme 作用下， 以 aq. acetate buffer 为溶剂， 反应 0.25h， 生成 9S,10S-trans-epoxy-11S-threo-hydroxy-octadec-12Z-enoic acid
  参考文献：
  名称：

  Epoxyalcohol synthase of Ectocarpus siliculosus . First CYP74-related enzyme of oxylipin biosynthesis in brown algae

  摘要：

  Enzymes of CYP74 family play the central role in the biosynthesis of physiologically important oxylipins in land plants. Although a broad diversity of oxylipins is known in the algae, no CYP74s or related enzymes have been detected in brown algae yet. Cloning of the first CYP74-related gene CYP5164B1 of brown alga Ectocarpus siliculosus is reported in present work. The recombinant protein was incubated with several fatty acid hydroperoxides. Linoleic acid 9-hydroperoxide (9-HPOD) was the preferred substrate, while linoleate 13-hydroperoxide (13-HPOD) was less efficient. a.-Linolenic acid 9- and 13-hydroperoxides, as well as eicosapentaenoic acid 15-hydroperoxide were inefficient substrates. Both 9-HPOD and 13-HPOD were converted into epoxyalcohols. For instance, 9-HPOD was turned primarily into (9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid. Both epoxide and hydroxyl oxygen atoms of the epoxyalcohol were incorporated mostly from [O-18(2)]9-HPOD. Thus, the enzyme exhibits the activity of epoxyalcohol synthase (EsEAS). The results show that the EsEAS isomerizes the hydroperoxides into epoxyalcohols via epoxyallylic radical, a common intermediate of different CYP74s and related enzymes. EsEAS can be considered as an archaic prototype of CYP74 family enzymes. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.bbalip.2016.11.007

文献信息

• Steric analysis of epoxyalcohol and trihydroxy derivatives of 9-hydroperoxy-linoleic acid from hematin and enzymatic synthesis
  作者：Christopher P. Thomas、William E. Boeglin、Yoel Garcia-Diaz、Valerie B. O’Donnell、Alan R. Brash

  DOI：10.1016/j.chemphyslip.2013.01.002

  日期：2013.2

  analysis of dimethoxypropane derivatives. Four trihydroxy isomers were identified upon mild acid hydrolysis of 9S,10S-trans-epoxy-11E-13S-hydroxyoctadecenoate: 9S,10R,13S, 9S,12R,13S, 9S,10S,13S and 9S,12S,13S-trihydroxy-octadecenoic acids, in the ratio 40:26:22:12. We also identified a prominent δ-ketol rearrangement product from the hydrolysis as mainly the 9-hydroxy-10E-13-oxo isomer. Short incubation

  我们表征从9产生的烯丙基环氧醇以及它们的三羟基的水解产物- [R -和9 š非酶促条件下-hydroperoxy十八碳烯酸（HPODE）中，用羟高铁血红素和随后的酸水解反应和酶的条件下，温育与甜菜含有氢过氧化物异构酶和环氧化物水解酶。产物通过 HPLC 解析，转化的区域和立体化学通过1 H NMR 和 GC-MS 分析二甲氧基丙烷衍生物的组合来确定。9 S ,10 S - trans -epoxy-11 E -13 的弱酸水解鉴定出四种三羟基异构体S-羟基十八烯酸：9 S ,10 R ,13 S , 9 S ,12 R ,13 S , 9 S ,10 S ,13 S和 9 S ,12 S ,13 S-三羟基-十八碳烯酸，比例为 40: 26:22:12。我们还从水解中确定了一个突出的 δ-酮醇重排产物，主要是 9-羟基-10 E -13-氧代异构体。9 R-和 9 S -HPODE 与B.