Design and synthesis of novel prostaglandin E 2 ethanolamide and glycerol ester probes for the putative prostamide receptor(s)

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 positio...

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Bibliographic Details
Published in:Tetrahedron letters 2015-03, Vol.56 (11), p.1411
Main Authors: Shelnut, Erin L, Nikas, Spyros P, Finnegan, David F, Chiang, Nan, Serhan, Charles N, Makriyannis, Alexandros
Format: Article
Language:English
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Summary: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.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2015.01.164