(4R,5S)-3-[(2S,3S,4S,6S,7S,10S,11S)-3-hydroxy-4-methyl-2,6,10-triethyl-6,7;10,11-diepoxydodecanoyl]-4-methyl-5-phenyl-2-oxazolidinone | 1227153-93-6

• 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: (4R,5S)-3-[(2S,3S,4S,6S,7S,10S,11S)-3-hydroxy-4-methyl-2,6,10-triethyl-6,7;10,11-diepoxydodecanoyl]-4-methyl-5-phenyl-2-oxazolidinone
• CAS: 1227153-93-6
• 化学式: C₂₉H₄₃NO₆
• 分子量: 501.664
• InChiKey: PLMSSXURLNIBST-QXOGNLIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  36.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  91.9
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-[(2S,3S,4S,6S,7S,10S,11S)-3-hydroxy-4-methyl-2,6,10-triethyl-6,7;10,11-diepoxydodecanoyl]-4-methyl-5-phenyl-2-oxazolidinone 在 水 、 三氯乙酸 作用下， 反应 6.0h， 生成 (4R,5S)-3-[(2S,3S,4S,6R,7S,10R,11S)-11-hydroxy-4-methyl-2,6,10-triethyl-3,6;7,10-diepoxydodecanoyl]-4-methyl-5-phenyl-2-oxazolidinone
  参考文献：
  名称：

  Intriguing Substrate Tolerance of Epoxide Hydrolase Lsd19 Involved in Biosynthesis of the Ionophore Antibiotic Lasalocid A

  摘要：

  Recently, we reported that the epoxide hydrolase Lsd19, the first enzyme shown to catalyze epoxide-opening cascades, can catalyze the conversion of a putative bisepoxide intermediate to polyether antibiotic lasalocid, which involves energetically disfavored 6-endo-tet cyclization of the epoxy alcohol. Here, we examined the substrate tolerance of Lsd19. Lsd19 accepts various substrate analogues differing in the left segment of lasalocid and epoxide stereochemistry to afford either THF-THP or THF-THF products with excellent regioselectivity.

  DOI：

  10.1021/ol100541e
• 作为产物：
  描述：

  (4R,5S)-3-[(2S,3S,4S,6S,7S,10S,11S)-4-methyl-2,6,10-triethyl-3-triethylsiloxy-6,7;10,11-diepoxydodecanoyl]-4-methyl-5-phenyl-2-oxazolidinone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以36%的产率得到(4R,5S)-3-[(2S,3S,4S,6S,7S,10S,11S)-3-hydroxy-4-methyl-2,6,10-triethyl-6,7;10,11-diepoxydodecanoyl]-4-methyl-5-phenyl-2-oxazolidinone
  参考文献：
  名称：

  Intriguing Substrate Tolerance of Epoxide Hydrolase Lsd19 Involved in Biosynthesis of the Ionophore Antibiotic Lasalocid A

  摘要：

  Recently, we reported that the epoxide hydrolase Lsd19, the first enzyme shown to catalyze epoxide-opening cascades, can catalyze the conversion of a putative bisepoxide intermediate to polyether antibiotic lasalocid, which involves energetically disfavored 6-endo-tet cyclization of the epoxy alcohol. Here, we examined the substrate tolerance of Lsd19. Lsd19 accepts various substrate analogues differing in the left segment of lasalocid and epoxide stereochemistry to afford either THF-THP or THF-THF products with excellent regioselectivity.

  DOI：

  10.1021/ol100541e