Erin L Shelnut1, Spyros P Nikas1, David F Finnegan1, Nan Chiang2, Charles N Serhan2, Alexandros Makriyannis3. 1. 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. 2. 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. 3. 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 ; King Abdulaziz University, Jeddah 22254, Saudi Arabia.
Abstract
Novel prostaglandin-ethanolamide (PGE2-EA) and glycerol ester (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 Mitsunobu azidation and peptide coupling as the key steps. A chemoenzymatic synthesis for the 2-PGE2-G is described for first time.
Novel prostaglandin-ethanolamide (n class="Chemical">PGE2-EA) and glycerol ester (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 Mitsunobu azidation and peptide coupling as the key steps. A chemoenzymatic synthesis for the 2-PGE2-G is described for first time.
Authors: Robert P Picone; Atmaram D Khanolkar; Wei Xu; Lionel A Ayotte; Ganesh A Thakur; Dow P Hurst; Mary E Abood; Patricia H Reggio; Donna J Fournier; Alexandros Makriyannis Journal: Mol Pharmacol Date: 2005-09-12 Impact factor: 4.436
Authors: C N Serhan; J F Maddox; N A Petasis; I Akritopoulou-Zanze; A Papayianni; H R Brady; S P Colgan; J L Madara Journal: Biochemistry Date: 1995-11-07 Impact factor: 3.162
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