title: Chiral liquid chromatography separation and chiroptical properties of the enantiomers of dimethyl alpha-hydroxyfarnesylphosphonate, a precursor of a farnesyl protein transferase inhibitor.
abstract: The HPLC enantiomeric separation of racemic and non-racemic samples of dimethyl alpha-hydroxyfarnesylphosphonate (1) was accomplished using Chiralcel OD as chiral stationary phase. Single enantiomers were isolated by semipreparative HPLC and their CD spectra and optical rotations were measured. The method ascertains enantiomeric excess of 1, obtained by oxidation of dimethylfarnesylphosphonate with enantiopure oxaziridines, avoiding converting the enantiomers to diastereomers by the use of a chiral auxiliary. Stability of the solutions of 1 is strongly dependent on the nature of the solvent.
authors.affiliation: Dipartimento di Scienze Chimiche, Università di Catania, Italy. scaccamese@dipchi.unict.it
authors.forename: Salvatore
authors.initials: S
authors.lastname: Caccamese
authors.forename: Giovanna
authors.initials: G
authors.lastname: Scivoli
authors.forename: Yanming
authors.initials: Y
authors.lastname: Du
authors.forename: David F
authors.initials: DF
authors.lastname: Wiemer
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002942:Circular Dichroism; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism