Analytical and preparative resolution of enantiomers of prostaglandin precursors and prostaglandins by liquid chromatography on derivatized cellulose chiral stationary phases.
Analytical methods were developed for the separation of the enantiomers of four cyclopentenone precursors of prostaglandins. The resolution obtained is correlated with the chemical environment around the chiral center of the cyclopentenones. The analytical methods were scaled up to preparative loadings and the chromatographic parameters were varied to determine their effect on the preparative separations. The correlation between analytical resolution and preparative resolution was also investigated. In addition to the precursors, the preparative resolution of the enantiomers of a synthetic prostaglandin analogue was investigated.
Miller
L
L
Chemical Development Department, G.D. Searle & Co., Skokie, IL 60077.
Weyker
C
C
D000527:Alprostadil / Q000031:analogs & derivatives / Q000302:isolation & purification; D002482:Cellulose; D002851:Chromatography, High Pressure Liquid; D002853:Chromatography, Liquid; D008968:Molecular Conformation; D011453:Prostaglandins / Q000032:analysis / Q000302:isolation & purification*; D012997:Solvents; D013237:Stereoisomerism
D011453:Prostaglandins; D012997:Solvents; D002482:Cellulose; D000527:Alprostadil; C054594:enisoprost