prostaglandin E₂ glycerol ester | 309260-53-5

• 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: prostaglandin E₂ glycerol ester
• 英文别名: (5Z,11α,13E,15S)-11,15-dihydroxy-9-oxo-prosta-5,13-dien-1-oic-1,3-dihydroxypropan-2-yl ester；prostaglandin E₂ -glycerol；PGE₂-G；2-glyceryl-Prostaglandin E2；1,3-dihydroxypropan-2-yl (Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoate
• CAS: 309260-53-5
• 化学式: C₂₃H₃₈O₇
• 分子量: 426.551
• InChiKey: HJWDPZIOTMUWRW-CXZSOYKBSA-N

物化性质

• 沸点：
  618.1±55.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (Z)-7-((1R,2R,3R,5S)-3-((tert-butyldimethylsilyl)oxy)-2-((S,E)-3-((tert-butyldimethylsilyl)oxy)oct-1-en-1-yl)-5-hydroxycyclopentyl)hept-5-enoic acid 在 吡啶 、 盐酸 、 lipase from Candida rugosa type VII 、 戴斯-马丁氧化剂 、 N,N'-羰基二咪唑 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 29.08h， 生成 prostaglandin E₂ glycerol ester
  参考文献：
  名称：

  推定的前列腺素受体的新型前列腺素E 2乙醇酰胺和甘油酯探针的设计与合成

  摘要：

  设计并合成了新的前列腺素-乙醇酰胺（PGE 2 -EA）和甘油酯（2-PGE 2 -G）类似物，以辅助推定的前列腺酰胺受体的表征。我们的设计在原型的终端尾部位置结合了亲电异硫氰酸根合基团和可光活化的叠氮基团。立体选择性Wittig和Horner–Wadsworth–Emmons反应会安装PGE 2骨架的头部和尾部。使用Mitsunobu叠氮化和肽偶联作为关键步骤完成了合成。首次描述了2-PGE 2 -G的化学酶法合成。

  DOI：

  10.1016/j.tetlet.2015.01.164

文献信息

• Metabolism of the Endocannabinoids, 2-Arachidonylglycerol and Anandamide, into Prostaglandin, Thromboxane, and Prostacyclin Glycerol Esters and Ethanolamides
  作者：Kevin R. Kozak、Brenda C. Crews、Jason D. Morrow、Lee-Ho Wang、Y. Henry Ma、Rolf Weinander、Per-Johan Jakobsson、Lawrence J. Marnett

  DOI：10.1074/jbc.m206788200

  日期：2002.11

  Cyclooxygenase-2 (COX-2) action on the endocannabinoids, 2-arachidonylglycerol (2-AG) and anandamide (AEA), generates prostaglandin glycerol esters (PG-G) and ethanolamides (PG-EA), respectively. The diversity of PG-Gs and PG-EAs that can be formed enzymatically following COX-2 oxygenation of endocannabinoids was examined in cellular and subcellular systems. In cellular systems, glycerol esters and ethanolamides of PGE(2), PGD(2), and PGF(2alpha) were major products of the endocannabinoid-derived COX-2 products, PGH(2)-G and PGH(2)-EA. The sequential action of purified COX-2 and thromboxane synthase on AEA and 2-AG provided thromboxane A(2) ethanolamide and glycerol ester, respectively. Similarly, bovine prostacyclin synthase catalyzed the isomerization of the intermediate endoperoxides, PGH(2)-G and PGH(2)-EA, to the corresponding prostacyclin derivatives. Quantification of the efficiency of prostaglandin and thromboxane synthase-directed endoperoxide isomerization demonstrated that PGE, PGD, and PGI synthases catalyze the isomerization of PGH(2)-G at rates approaching those observed with PGH(2). In contrast, thromboxane synthase was far more efficient at catalyzing PGH(2) isomerization than at catalyzing the isomerization of PGH(2)-G. These results define the in vitro diversity of endocannabinoid-derived prostanoids and will permit focused investigations into their production and potential biological actions in vivo.
• Design and synthesis of novel prostaglandin E2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s)
  作者：Erin L. Shelnut、Spyros P. Nikas、David F. Finnegan、Nan Chiang、Charles N. Serhan、Alexandros Makriyannis

  DOI：10.1016/j.tetlet.2015.01.164

  日期：2015.3

  (2-PGE2-G) analogs were designed and synthesized to aid in the characterization of a putative prostamide receptor. Our design incorporates the electrophilic isothiocyanato and the photoactivatable azido groups at the terminal tail position of the prototype. Stereoselective Wittig and Horner–Wadsworth–Emmons reactions install the head and the tail moieties of the PGE2 skeleton. The synthesis is completed using

  设计并合成了新的前列腺素-乙醇酰胺（PGE 2 -EA）和甘油酯（2-PGE 2 -G）类似物，以辅助推定的前列腺酰胺受体的表征。我们的设计在原型的终端尾部位置结合了亲电异硫氰酸根合基团和可光活化的叠氮基团。立体选择性Wittig和Horner–Wadsworth–Emmons反应会安装PGE 2骨架的头部和尾部。使用Mitsunobu叠氮化和肽偶联作为关键步骤完成了合成。首次描述了2-PGE 2 -G的化学酶法合成。