5-(S)-HPETE methyl ester | 75331-81-6

• 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: 5-(S)-HPETE methyl ester
• 英文别名: (S)-5-hydroperoxy-6-trans,8,11,14-cis-eicosatetraenoic acid methyl ester；Methyl 5(S)-hydroperoxy-6(E),8(Z),11(Z),14(Z)-eicosatetraenoate；methyl (5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoate
• CAS: 75331-81-6
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: OUXFZOQEFZZSHQ-KPMWKZHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(S)-HPETE methyl ester 在 三苯基膦 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以80%的产率得到5(S)-HETE methyl ester
  参考文献：
  名称：

  A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE

  摘要：

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.

  DOI：

  10.1021/jo00106a037
• 作为产物：
  描述：

  花生四烯酸 在 potato lipoxygenase 氧气 、 potassium carbonate 作用下， 以 乙醚 为溶剂， 反应 0.24h， 生成 5-(S)-HPETE methyl ester
  参考文献：
  名称：

  Stereochemistry and mechanism of the biosynthesis of leukotriene A4 from 5(S)-hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic acid. Evidence for an organoiron intermediate

  摘要：

  DOI：

  10.1021/ja00186a046

文献信息

• Synthesis of the slow reacting substance of anaphylaxis leukotriene C-1 from arachidonic acid
  作者：E. J. Corey、Alan E. Barton、David A. Clark

  DOI：10.1021/ja00532a059

  日期：1980.6
• Stereochemistry and mechanism of the biosynthesis of leukotriene A4 from 5(S)-hydroperoxy-6(E),8,11,14(Z)-eicosatetraenoic acid. Evidence for an organoiron intermediate
  作者：E. J. Corey、Stephen W. Wright、Seiichi P. T. Matsuda

  DOI：10.1021/ja00186a046

  日期：1989.2
• A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE
  作者：Patrick Dussault、In Quen Lee

  DOI：10.1021/jo00106a037

  日期：1995.1

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.