Design and synthesis of novel prostaglandin E₂ ethanolamide 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 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.

SUBMITTER: Shelnut EL 

PROVIDER: S-EPMC4422110 | biostudies-literature | 2015 Mar

REPOSITORIES: biostudies-literature