Conformational and temperature effects on separation of stereoisomers of a C3,C4-substituted beta-lactamic cholesterol absorption inhibitor on amylose-based chiral stationary phases.
A direct liquid chromatography method was developed for the diastereo- and enantioselective analysis of a C3,C4-substituted beta-lactamic hypolipodemic agent (SCH 48461) and its stereoisomers on two commercially available amylose-based chiral stationary phases (CSPs), namely, Chiralpak AS and Chiralpak AD. The mobile phase composition (type and content of alcoholic modifier) was considered to achieve baseline resolutions in a single chromatographic run. In order to investigate the influence of molecular flexibility on chiral recognition process, beta-lactams were ring-opened and converted into beta-amino esters derivatives. Thermodynamic parameters associated with adsorption equilibria between acyclic and cyclic stereoisomers and CSPs were calculated from chromatographic runs at various temperatures.
Cirilli
R
R
Istituto Superiore di Sanità, Laboratorio di Chimica del Farmaco, Rome, Italy.
Del Giudice
M R
MR
Ferretti
R
R
La Torre
F
F
D000688:Amylose / Q000031:analogs & derivatives* / Q000737:chemistry; D000924:Anticholesteremic Agents / Q000032:analysis / Q000737:chemistry; D001384:Azetidines / Q000032:analysis / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D008968:Molecular Conformation; D048448:Phenylcarbamates; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics; D047090:beta-Lactams / Q000737:chemistry*
D000924:Anticholesteremic Agents; D001384:Azetidines; D002219:Carbamates; D048448:Phenylcarbamates; D047090:beta-Lactams; C445088:chiralpak AS; C080033:Chiralpak AD; C095487:1,4-bis(4-methoxyphenyl)-3-(3-phenylpropyl)-2-azetidinone; D000688:Amylose