用于假定前列腺酰胺受体的新型前列腺素E乙醇酰胺和甘油酯探针的设计与合成。
Design and synthesis of novel prostaglandin E ethanolamide and glycerol ester probes for the putative prostamide receptor(s).
作者信息
Shelnut Erin L, Nikas Spyros P, Finnegan David F, Chiang Nan, Serhan Charles N, Makriyannis Alexandros
机构信息
Center for Drug Discovery and Departments of Chemistry and Chemical Biology and Pharmaceutical Sciences, Northeastern University, 360 Huntington Ave, 116 Mugar Hall, Boston, MA 02115, USA.
Center for Experimental Therapeutics and Reperfusion Injury, Department of Anesthesiology, Perioperative and Pain Medicine, Harvard Institutes of Medicine, 77 Avenue Louis Pasteur (HIM 829), Brigham and Women's Hospital and Harvard Medical School, Boston, MA 02115, USA.
出版信息
Tetrahedron Lett. 2015 Mar 11;56(11):1411-1415. doi: 10.1016/j.tetlet.2015.01.164.
Novel prostaglandin-ethanolamide (PGE-EA) and glycerol ester (2-PGE-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 PGE skeleton. The synthesis is completed using Mitsunobu azidation and peptide coupling as the key steps. A chemoenzymatic synthesis for the 2-PGE-G is described for first time.
设计并合成了新型前列腺素 - 乙醇酰胺（PGE - EA）和甘油酯（2 - PGE - G）类似物，以帮助鉴定一种假定的前列腺酰胺受体。我们的设计在原型的末端尾部位置引入了亲电异硫氰酸酯和光可活化的叠氮基。立体选择性维蒂希反应和霍纳 - 沃兹沃思 - 埃蒙斯反应构建了PGE骨架的头部和尾部部分。合成以 Mitsunobu 叠氮化反应和肽偶联作为关键步骤完成。首次描述了2 - PGE - G的化学酶促合成方法。
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