(5S)-(-)-<2-(2)H2,5-(2)H>-5-Hydroxyoctanoyl methyl ester | 168207-68-9

• 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: (5S)-(-)-<2-(2)H2,5-(2)H>-5-Hydroxyoctanoyl methyl ester
• 英文别名: methyl (5S)-2,2,5-trideuterio-5-hydroxyoctanoate
• CAS: 168207-68-9
• 化学式: C₉H₁₈O₃
• 分子量: 177.216
• InChiKey: XMQPWFCBPDENRU-PZDLWJPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S)-(-)-<2-(2)H2,5-(2)H>-5-Hydroxyoctanoyl methyl ester 在 咪唑 、 三甲基铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 72.25h， 生成 (5S)-(-)-<2-(2)H2,5-(2)H>-5-<(tert-Butyldimethylsilyl)oxy>octanoyl NAC thioester
  参考文献：
  名称：

  Biosynthesis of the Hypotensive Metabolite Oudenone by Oudemansiella radicata. 1. Intact Incorporation of a Tetraketide Chain Elongation Intermediate

  摘要：

  The biosynthesis of the fungal metabolite oudenone (1) was investigated in cultures of Oudemansiella radicata. Feeding experiments using C-13 and H-2-labeled precursors, as well as NMR analyses of the labeled metabolite, suggested a polyketide origin. The incorporation of six acetate units into the carbon skeleton of 1 was observed when cultures were fed the N-acetylcysteamine thioester derivative of C-13-labeled acetate. Labeling of oudenone (1) from [1,4-C-13(2)]succinate or L-[5-C-13]-glutamic acid was not observed, whereas the pattern of C-13 labeling from [2,3-C-13(2)]succinate was identical to that observed with [1,2-C-13(2)]acetate. The proposed advanced intermediate (5S)-5-hydroxyoctanoic acid (2) was synthesized as the deuterium labeled N-acetylcysteamine thioester derivative (S)-19 and successfully incorporated into 1. A biosynthetic scheme and cyclization mechanism, consistent with the experimental data, is proposed.

  DOI：

  10.1021/jo00126a050
• 作为产物：
  描述：

  甲醇 、 (3S)-(-)-<3-(2)H,6-(2)H2>-3-Propyl-δ-valerolactone 在 camphor-10-sulfonic acid 作用下， 反应 12.0h， 以96%的产率得到(5S)-(-)-<2-(2)H2,5-(2)H>-5-Hydroxyoctanoyl methyl ester
  参考文献：
  名称：

  Biosynthesis of the Hypotensive Metabolite Oudenone by Oudemansiella radicata. 1. Intact Incorporation of a Tetraketide Chain Elongation Intermediate

  摘要：

  The biosynthesis of the fungal metabolite oudenone (1) was investigated in cultures of Oudemansiella radicata. Feeding experiments using C-13 and H-2-labeled precursors, as well as NMR analyses of the labeled metabolite, suggested a polyketide origin. The incorporation of six acetate units into the carbon skeleton of 1 was observed when cultures were fed the N-acetylcysteamine thioester derivative of C-13-labeled acetate. Labeling of oudenone (1) from [1,4-C-13(2)]succinate or L-[5-C-13]-glutamic acid was not observed, whereas the pattern of C-13 labeling from [2,3-C-13(2)]succinate was identical to that observed with [1,2-C-13(2)]acetate. The proposed advanced intermediate (5S)-5-hydroxyoctanoic acid (2) was synthesized as the deuterium labeled N-acetylcysteamine thioester derivative (S)-19 and successfully incorporated into 1. A biosynthetic scheme and cyclization mechanism, consistent with the experimental data, is proposed.

  DOI：

  10.1021/jo00126a050