Separation of cis-beta-lactam enantiomers by capillary electrophoresis using cyclodextrin derivatives.
Chiral separation of 19 pairs of cis-beta-lactam (BL) stereoisomers of pharmacological importance was examined by capillary electrophoresis using cyclodextrin (CD) derivatives. In order to select the most effective conditions separating the highest number of stereoisomers of BLs, single carboxymethyl alpha-, beta- and gamma-, as well as sulfobutyl beta-CD derivatives were applied. Additionally, carboxymethyl and sulfobutyl beta-CD derivatives complemented with neutral beta-CD derivatives as dual CD systems were tested. Both the composition and concentration of applied selectors and the pH of background electrolyte were selected. In single systems the structural characteristics of BLs and the complex forming affinity were correlated. Most BLs provided optimal complexation with beta-CD derivatives. In conclusion, the efficiency of combining sulfobutyl-beta-CD and permethylated beta-CD was superior to other single and dual CD systems applied. This method successfully separated each pair of stereoisomers investigated.
Németh
Krisztina
K
Institute of Biomolecular Chemistry, Chemical Research Center, Hungarian Academy of Sciences, H-1525 Budapest, POB 17, Hungary.
Varga
Erzsébet
E
Iványi
Róbert
R
Szemán
Julianna
J
Visy
Júlia
J
Jicsinszky
László
L
Szente
Lajos
L
Forró
Eniko
E
Fülöp
Ferenc
F
Péter
Antal
A
Simonyi
Miklós
M
D004355:Drug Stability; D019075:Electrophoresis, Capillary / Q000379:methods*; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*; D047090:beta-Lactams / Q000032:analysis / Q000737:chemistry*
D047392:beta-Cyclodextrins; D047090:beta-Lactams; C031215:betadex