methyl (9R,10S)-epoxy-12-octadecenoate | 6084-72-6

• 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: methyl (9R,10S)-epoxy-12-octadecenoate
• 英文别名: (+/-)-cis-9,10-Epoxy-12(Z)-octadecenoic acid methyl ester；methyl 8-[(2R,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]octanoate
• CAS: 6084-72-6
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: JCJMEMDHUZYVMB-OPEQHFAOSA-N

物化性质

• 沸点：
  384.8±15.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 (Z,Z)-9,12-十八烷二烯酸二聚物 在 过氧化氢异丙苯 、 recombinant caleosin PXG₄ from Arabidopsis thaliana 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 methyl 8-(3-((3-pentyloxiran-2-yl)methyl)oxiran-2-yl)octanoate 、 methyl (9R,10S)-epoxy-12-octadecenoate 、 (-)-leukotoxin B methyl ester
  参考文献：
  名称：

  A non-canonical caleosin fromArabidopsisefficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity

  摘要：

  In plants, epoxygenated fatty acids (EFAs) are constituents of oil seeds as well as defence molecules and components of biopolymers (cutin, suberin). While the pleiotropic biological activities of mammalian EFAs have been well documented, there is a paucity of information on the physiological relevance of plant EFAs and their biosynthesis. Potential candidates for EFA formation are caleosin‐type peroxygenases which catalyze the epoxidation of unsaturated fatty acids in the presence of hydroperoxides as co‐oxidants. However, the caleosins characterized so far, which are mostly localized in seeds, are poor epoxidases. In sharp contrast, quantitative RT‐PCR analysis revealed that PXG4, a class II caleosin gene, is expressed in roots, stems, leaves and flowers of Arabidopsis. Expressed in yeast, PXG4 encodes a calcium‐dependent membrane‐associated hemoprotein able to catalyze typical peroxygenase reactions. Moreover, we show here that purified recombinant PXG4 is an efficient fatty acid epoxygenase, catalyzing the oxidation of cis double bonds of unsaturated fatty acids. Physiological linoleic and linolenic acids proved to be the preferred substrates for PXG4; they are oxidized into the different positional isomers of the monoepoxides and into diepoxides. An important regioselectivity was observed; the C‐12,13 double bond of these unsaturated fatty acids being the least favored unsaturation epoxidized by PXG4, linolenic acid preferentially yielded the 9,10‐15,16‐diepoxide. Remarkably, PXG4 catalyzes exclusively the formation of (R),(S)‐epoxide enantiomers, which is the absolute stereochemistry of the epoxides found in planta. These findings pave the way for the study of the functional role of EFAs and caleosins in plants.

  DOI：

  10.1111/j.1742-4658.2012.08757.x