(R)-N-(2,3-dihydroxypropyl)stearamide | 955998-69-3

• 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: (R)-N-(2,3-dihydroxypropyl)stearamide
• 英文别名: N-[(2R)-2,3-dihydroxypropyl]octadecanamide
• CAS: 955998-69-3
• 化学式: C₂₁H₄₃NO₃
• 分子量: 357.577
• InChiKey: ILMOLWSTFFMGGB-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  25
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-N-(2,3-dihydroxypropyl)stearamide 在 吡啶 、 4-二甲氨基吡啶 、 三甲基乙酰氯 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-(2-O-benzoyl-1-N-stearamido-sn-glycerol) (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phosphate triethylammonium salt
  参考文献：
  名称：

  Preference for Glucose over Inositol Headgroup during Lysolipid Activation of G Protein-Coupled Receptor 55

  摘要：

  G protein-coupled receptor 55 (GPR55) is highly expressed in brain and chemorepulsion peripheral nervous system. Originally deorphanized as a cannabinoid receptor, recently GPRS5 has been described as a lysophospholipid-responsive receptor, specifically toward lysophosphatidylinositol and lysophosphatidyl-beta-n-glucoside (LysoPtdGlc). To characterize lysolipid-GPR55 interaction, synthetic access to LysoPtdGlc and selected analogues was established utilizing a phosphorus(III)-based chemical approach. The biological activity of each synthetic lipid was assessed using a GPR55-dependent chemotropism assay in primary sensory neurons. Combined with molecular dynamics simulations the potential ligand entry port and binding pocket specifics are discussed. These results highlight the preference for gluco- over inositol- and galacto-configured headgroups.

  DOI：

  10.1021/acschemneuro.8b00505
• 作为产物：
  描述：

  (R)-3-氨基-1,2-丙二醇 、 十八烷酰氯 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以58%的产率得到(R)-N-(2,3-dihydroxypropyl)stearamide
  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

文献信息

• [EN] PHOSPHOLIPID COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS PHOSPHOLIPIDIQUES ET LEURS UTILISATIONS
  申请人：GILEAD SCIENCES INC

  公开号：WO2022081973A1

  公开（公告）日：2022-04-21

  Compounds and methods of using said compounds, alone or in combination with additional agents, and pharmaceutical compositions of said compounds for the treatment of viral infections are disclosed.

  本文披露了用于治疗病毒感染的化合物及其使用方法，可以单独使用或与其他药物联合使用，并且还包括该化合物的药物组合物。
• Synthesis and Evaluation of Lysophosphatidylserine Analogues as Inducers of Mast Cell Degranulation. Potent Activities of Lysophosphatidylthreonine and Its 2-Deoxy Derivative
  作者：Masazumi Iwashita、Kumiko Makide、Taro Nonomura、Yoshimasa Misumi、Yuko Otani、Mayuko Ishida、Ryo Taguchi、Masafumi Tsujimoto、Junken Aoki、Hiroyuki Arai、Tomohiko Ohwada

  DOI：10.1021/jm900598m

  日期：2009.10.8

  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.
• PHOSPHOLIPID COMPOUNDS AND USES THEREOF
  申请人：Gilead Sciences, Inc.

  公开号：US20220143052A1

  公开（公告）日：2022-05-12

  Compounds and methods of using said compounds, alone or in combination with additional agents, and pharmaceutical compositions of said compounds for the treatment of viral infections are disclosed.
• Preference for Glucose over Inositol Headgroup during Lysolipid Activation of G Protein-Coupled Receptor 55
  作者：Adam T. Guy、Koki Kano、Jyunpei Ohyama、Hiroyuki Kamiguchi、Yoshio Hirabayashi、Yukishige Ito、Ichiro Matsuo、Peter Greimel

  DOI：10.1021/acschemneuro.8b00505

  日期：2019.1.16

  G protein-coupled receptor 55 (GPR55) is highly expressed in brain and chemorepulsion peripheral nervous system. Originally deorphanized as a cannabinoid receptor, recently GPRS5 has been described as a lysophospholipid-responsive receptor, specifically toward lysophosphatidylinositol and lysophosphatidyl-beta-n-glucoside (LysoPtdGlc). To characterize lysolipid-GPR55 interaction, synthetic access to LysoPtdGlc and selected analogues was established utilizing a phosphorus(III)-based chemical approach. The biological activity of each synthetic lipid was assessed using a GPR55-dependent chemotropism assay in primary sensory neurons. Combined with molecular dynamics simulations the potential ligand entry port and binding pocket specifics are discussed. These results highlight the preference for gluco- over inositol- and galacto-configured headgroups.