(-)-leukotoxin B methyl ester | 105229-02-5

• 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: (-)-leukotoxin B methyl ester
• 英文别名: methyl (12R,13S)-epoxyoleate；(-)-12(R),13(S)-vernolic acid methyl ester；methyl (12R,13S)-epoxy-9-octadecenoate；Vernolic acid methyl ester；methyl (Z)-11-[(2R,3S)-3-pentyloxiran-2-yl]undec-9-enoate
• CAS: 105229-02-5
• 化学式: C₁₉H₃₄O₃
• 分子量: 310.477
• InChiKey: JTSVQVYMBXVLFI-IPASSIEDSA-N

物化性质

• 沸点：
  391.7±25.0 °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

• 作为反应物：
  描述：

  (-)-leukotoxin B methyl ester 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 12,13-Epoxylinoleic acid
  参考文献：
  名称：

  Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

  摘要：

  Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S), 15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4039(01)00694-3
• 作为产物：
  描述：

  (9Z)-11-[(2S,3R)-3-戊基-2-环氧乙烷基]-9-十一碳烯酸甲酯 在 三乙烯二胺 、 aluminum oxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 二丁醚 、 乙腈 为溶剂， 反应 62.0h， 生成 (-)-leukotoxin B methyl ester
  参考文献：
  名称：

  Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)

  摘要：

  Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S), 15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4039(01)00694-3

文献信息

• A non-canonical caleosin from<i>Arabidopsis</i>efficiently epoxidizes physiological unsaturated fatty acids with complete stereoselectivity
  作者：Elizabeth Blée、Martine Flenet、Benoît Boachon、Marie-Laure Fauconnier

  DOI：10.1111/j.1742-4658.2012.08757.x

  日期：2012.10

  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.
• Synthesis of 12(R),13(S)-oxido-9-octadecenoic (vernolic) and 13(S)-hydroxy-9, 11-octadecadienoic (coriolic) acids
  作者：Christine A. Moustakis、D.K. Weerasinghe、Paul Mosset、J.R. Falck、Charles Mioskowski

  DOI：10.1016/s0040-4039(00)84002-2

  日期：1986.1
• GUNSTONE F. D.; SCHULER H. R., CHEM. AND PHYS. LIPIDS <CHIN-AG>, 1975, 15, NO 2, 174-188
  作者：GUNSTONE F. D.、 SCHULER H. R.

  DOI：——

  日期：——
• Practical, enantiospecific syntheses of 14,15-EET and leukotoxin B (vernolic acid)
  作者：J.R Falck、Y.Krishna Reddy、Donovan C Haines、Komandla Malla Reddy、U.Murali Krishna、Sandra Graham、Barbara Murry、Julian A Peterson

  DOI：10.1016/s0040-4039(01)00694-3

  日期：2001.6

  Cytochrome P450BM3 and its F87V mutant were exploited for a convenient, laboratory scale (1 mmol) preparation of 14(S), 15(R)-epoxyeicosatrienoic acid [14(S),15(R)-EET] from arachidonic acid and (+)-leukotoxin B [(+)-12(S),13(R)-vernolic acid] from linoleic acid, respectively. Their enantiomers were accessed via a four-step chemical inversion. (C) 2001 Elsevier Science Ltd. Ail rights reserved.