Enantiomeric separation of gemfibrozil chiral analogues by capillary electrophoresis with heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin as chiral selector.
The enantiomeric separation of gemfibrozil chiral analogues was performed by capillary zone electrophoresis (CZE). Resolution of the enantiomers was achieved using heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin (TM-beta-CD) as chiral selector dissolved into a buffer solution. In order to optimize the separation conditions, type, pH and concentration of running buffer and chiral selector concentration were varied. For each pH value, the optimum chiral selector concentration that produced the resolution of the isomers was found. The migration order of labile diastereoisomers formed was valued at the optimum experimental conditions by adding a pure optical isomer to the racemic mixture. Data from 1H NMR studies confirmed host-guest interaction between TM-beta-CD and 5-(2,5-dimethylphenoxy)-2-ethylpentanoic acid sodium salt. The hypothesized stoichiometry host:guest was 1:1. An apparent equilibrium constant (Ka) was estimated monitoring the chemical shift variation as a function of TM-beta-CD concentration. Salt effect on complexation equilibrium constant was also investigated.
Ammazzalorso
Alessandra
A
Dipartimento di Scienze del Farmaco, Università degli Studi G. d'Annunzio, via dei Vestini 31, 66100 Chieti, Italy.
Amoroso
Rosa
R
Bettoni
Giancarlo
G
Chiarini
Marco
M
De Filippis
Barbara
B
Fantacuzzi
Marialuigia
M
Giampietro
Letizia
L
Maccallini
Cristina
C
Tricca
Maria Luisa
ML
D002021:Buffers; D019075:Electrophoresis, Capillary / Q000379:methods*; D015248:Gemfibrozil / Q000737:chemistry / Q000302:isolation & purification*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
D002021:Buffers; D047392:beta-Cyclodextrins; C000609658:heptakis(2,3,6-tri-O-methyl)-beta-cyclodextrin; D015248:Gemfibrozil