(S)-3-hydroxy-2-(stearoyloxy)propyl phenyl succinate | 1514617-83-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (S)-3-hydroxy-2-(stearoyloxy)propyl phenyl succinate
• CAS: 1514617-83-4
• 化学式: C₃₁H₅₀O₇
• 分子量: 534.734
• InChiKey: IRMAHHOFONAPAF-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  38.0
• 可旋转键数：
  24.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  99.13
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-3-hydroxy-2-(stearoyloxy)propyl phenyl succinate 、 苄基N,N,N',N'-四异丙基亚磷酰二胺 在 四氮唑 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 以55%的产率得到(2R)-3-(benzyloxy(diisopropylamino)phosphinooxy)-2-(stearoyloxy)propyl phenyl succinate
  参考文献：
  名称：

  A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation

  摘要：

  We report the synthesis and biochemical validation of a phosphatidyl inositol-3 phosphate (PI3P) immunogen. The inositol stereochemistry was secured through peptide-catalyzed asymmetric phosphorylation catalysis, and the subsequent incorporation of a cysteine residue was achieved by native chemical ligation (NCL). Conjugation of the PI3P hapten to maleimide-activated keyhole limpet hemocyanin (KLH) provided a PI3P immunogen, which was successfully used to generate selective PI3P antibodies. The incorporation of a sulfhydryl nucleophile into a phosphoinositide hapten demonstrates a general strategy to reliably access phosphoinositide immunogens.

  DOI：

  10.1021/ja410750a
• 作为产物：
  描述：

  (S)-3-(4-methoxybenzyloxy)-2-(stearoyloxy)propyl phenyl succinate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以89%的产率得到(S)-3-hydroxy-2-(stearoyloxy)propyl phenyl succinate
  参考文献：
  名称：

  A Fully Synthetic and Biochemically Validated Phosphatidyl Inositol-3-Phosphate Hapten via Asymmetric Synthesis and Native Chemical Ligation

  摘要：

  We report the synthesis and biochemical validation of a phosphatidyl inositol-3 phosphate (PI3P) immunogen. The inositol stereochemistry was secured through peptide-catalyzed asymmetric phosphorylation catalysis, and the subsequent incorporation of a cysteine residue was achieved by native chemical ligation (NCL). Conjugation of the PI3P hapten to maleimide-activated keyhole limpet hemocyanin (KLH) provided a PI3P immunogen, which was successfully used to generate selective PI3P antibodies. The incorporation of a sulfhydryl nucleophile into a phosphoinositide hapten demonstrates a general strategy to reliably access phosphoinositide immunogens.

  DOI：

  10.1021/ja410750a