title: Design and synthesis of novel prostaglandin E2ethanolamide and glycerol ester probes for the putative prostamide receptor(s).
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 PGE2skeleton. 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.affiliation: 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.
authors.forename: Erin L
authors.initials: EL
authors.lastname: Shelnut
authors.affiliation: 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.
authors.forename: Spyros P
authors.initials: SP
authors.lastname: Nikas
authors.affiliation: 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.
authors.forename: David F
authors.initials: DF
authors.lastname: Finnegan
authors.affiliation: 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.
authors.forename: Nan
authors.initials: N
authors.lastname: Chiang
authors.affiliation: 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.
authors.forename: Charles N
authors.initials: CN
authors.lastname: Serhan
authors.affiliation: 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.
authors.forename: Alexandros
authors.initials: A
authors.lastname: Makriyannis
keywords: Endocannabinoids; Lipids; Prostaglandin glycerol ester; Prostamides