benzyl (2S,3R)-3-[[(2R)-3-hydroxy-2-phenylmethoxypropoxy]-phenylmethoxyphosphoryl]oxy-2-(phenylmethoxycarbonylamino)butanoate | 955948-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: benzyl (2S,3R)-3-[[(2R)-3-hydroxy-2-phenylmethoxypropoxy]-phenylmethoxyphosphoryl]oxy-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 955948-69-3
• 化学式: C₃₆H₄₀NO₁₀P
• 分子量: 677.688
• InChiKey: DCCPCDREVSJBEV-INOAEXKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3R)-3-[[(2R)-3-hydroxy-2-phenylmethoxypropoxy]-phenylmethoxyphosphoryl]oxy-2-(phenylmethoxycarbonylamino)butanoate 、 棕榈酰氯 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到[(2R)-3-[[(2R,3S)-4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butan-2-yl]oxy-phenylmethoxyphosphoryl]oxy-2-phenylmethoxypropyl] hexadecanoate
  参考文献：
  名称：

  Synthesis and Evaluation of Lysophosphatidylserine Analogues as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidylthreonine and Its 2-Deoxy Derivative

  摘要：

  In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs.

  DOI：

  10.1021/jm900598m
• 作为产物：
  描述：

  benzyl (2S,3R)-3-[[(2R)-3-(4-methoxyphenoxy)-2-phenylmethoxypropoxy]-phenylmethoxyphosphoryl]oxy-2-(phenylmethoxycarbonylamino)butanoate 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.33h， 以71%的产率得到benzyl (2S,3R)-3-[[(2R)-3-hydroxy-2-phenylmethoxypropoxy]-phenylmethoxyphosphoryl]oxy-2-(phenylmethoxycarbonylamino)butanoate
  参考文献：
  名称：

  Synthesis and Evaluation of Lysophosphatidylserine Analogues as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidylthreonine and Its 2-Deoxy Derivative

  摘要：

  In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs.

  DOI：

  10.1021/jm900598m