(2S)-3-[(4-stearoyloxybutoxy)-benzyloxyphosphoryloxy]-2-(benzyloxycarbonylamino)propionic acid benzyl ester | 955948-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-3-[(4-stearoyloxybutoxy)-benzyloxyphosphoryloxy]-2-(benzyloxycarbonylamino)propionic acid benzyl ester
• 英文别名: 4-[[(2S)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propoxy]-phenylmethoxyphosphoryl]oxybutyl octadecanoate
• CAS: 955948-35-3
• 化学式: C₄₇H₆₈NO₁₀P
• 分子量: 838.031
• InChiKey: FKWVTNINBCMGFN-SRSKHSKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  59
• 可旋转键数：
  37
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2S)-3-[(4-stearoyloxybutoxy)-benzyloxyphosphoryloxy]-2-(benzyloxycarbonylamino)propionic acid benzyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 24.0h， 以65%的产率得到(2S)-3-[(4-stearoyloxybutoxy)-hydroxyphosphoryloxy]-2-aminopropionic acid
  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：

  在 叔丁基过氧化氢 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以339.4 mg的产率得到(2S)-3-[(4-stearoyloxybutoxy)-benzyloxyphosphoryloxy]-2-(benzyloxycarbonylamino)propionic acid benzyl ester
  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