11α-[4,15-tetradeutero]-13β-acetoxy-2-ketoapotrichothecene | 226944-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 11α-[4,15-tetradeutero]-13β-acetoxy-2-ketoapotrichothecene
• CAS: 226944-86-1
• 化学式: C₁₇H₂₄O₄
• 分子量: 296.343
• InChiKey: ZFBAIBQNIPIOME-KSMKZOGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  11α-[4,15-tetradeutero]-13β-acetoxy-2-ketoapotrichothecene 在 甲醇 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 16.25h， 生成 11α-[4,15-tetradeutero]-2α,13β-apotrichodiol
  参考文献：
  名称：

  Biosynthesis of Trichothecenes and Apotrichothecenes

  摘要：

  Fusarium culmorum produces two major trilchothecenes, 3-acetyldeoxynivalenol and sambucinol, and some minor apotrichothecenes. It was desired to investigate if during their biosynthesis a C-11-keto intermediate was involved. To verify this postulate, trichodiene, a known precursor to trichothecenes, was synthesized with two deuteriums at C-11 and one at C-15. It was then fed to F. culmorum cultures, and the derived metabolites were purified and analyzed. The results ruled out the involvement of an 11-keto intermediate but revealed two novel apotrichothecenes. The characterization of their structures suggested that one of the 2-hydroxy-11 alpha-apotrichothecene stereoisomers (2 alpha or 2 beta) could be converted to sambucinol. These apotrichothecenes were therefore synthesized labeled specifically with two deuteriums at C-4 and C-15 and fed to F. culmorum cultures. Indeed, the result established for the first time that 2 alpha-hydroxy-11 alpha-apotriehothecene was a precursor to sambucinol. A biosynthetic scheme for the production of trichothecenes and apotrichothecenes is described.

  DOI：

  10.1021/jf980808r
• 作为产物：
  描述：

  11α-[4,15-tetradeutero]-13β-acetoxy-2β-apotricho-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以83%的产率得到11α-[4,15-tetradeutero]-13β-acetoxy-2-ketoapotrichothecene
  参考文献：
  名称：

  Biosynthesis of Trichothecenes and Apotrichothecenes

  摘要：

  Fusarium culmorum produces two major trilchothecenes, 3-acetyldeoxynivalenol and sambucinol, and some minor apotrichothecenes. It was desired to investigate if during their biosynthesis a C-11-keto intermediate was involved. To verify this postulate, trichodiene, a known precursor to trichothecenes, was synthesized with two deuteriums at C-11 and one at C-15. It was then fed to F. culmorum cultures, and the derived metabolites were purified and analyzed. The results ruled out the involvement of an 11-keto intermediate but revealed two novel apotrichothecenes. The characterization of their structures suggested that one of the 2-hydroxy-11 alpha-apotrichothecene stereoisomers (2 alpha or 2 beta) could be converted to sambucinol. These apotrichothecenes were therefore synthesized labeled specifically with two deuteriums at C-4 and C-15 and fed to F. culmorum cultures. Indeed, the result established for the first time that 2 alpha-hydroxy-11 alpha-apotriehothecene was a precursor to sambucinol. A biosynthetic scheme for the production of trichothecenes and apotrichothecenes is described.

  DOI：

  10.1021/jf980808r