title: Dehydration and epimerization of 7-thiaprostaglandin E1 analogues.
abstract: The kinetics of epimerization and dehydration of 7-thiaprostaglandin E1 (7-S-PGE1) analogues in various solvent systems were examined using HPLC. The epimerization at the C-8 position was rapid and resulted in a considerable amount of the 8-epimer (14-35%) at equilibrium. The dehydration was also rapid compared with that of the natural prostaglandin E1 (PGE1). The lability may be attributed to an effect of the sulfur atom substituted for the C-7 methylene.
mesh_terms: D000527:Alprostadil / Q000031:analogs & derivatives* / Q000032:analysis; D002021:Buffers; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002851:Chromatography, High Pressure Liquid; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D013237:Stereoisomerism
chemical_list: D002021:Buffers; C051204:20-dimethyl-7-thiaprostaglandin E1 methyl ester; C051203:15-cyclohexyl-omega-pentanor-7-thiaprostaglandin E1; D000527:Alprostadil