Comparison and modeling study of vancomycin, ristocetin A, and teicoplanin for CE enantioseparations

The structurally related glycopeptide antibiotics vancomycin, ristocetin A, and teicoplanin can all be used as chiral selectors in capillary electrophoresis (CE). Both experimental and modeling studies were done to elucidate their similarities and differences. There are identifiable morphological differences in the aglycon macrocyclic portions of these three compounds. In addition, there are other structural distinctions that can affect their CE enantioselectivity, migration times, and efficiency. Teicoplanin is the most distinct of the three and is the only one that is surface active. Its aggregational properties appear to affect its enantioselectivity among other things. The similar but not identical structures of the three glycopeptides produce similar but not identical enantioselectivities. This leads to the empirically useful "principle of complementary separations", in which a partial resolution with one chiral selector can be brought to baseline with one of the others. Overall, ristocetin A appears to have the greatest applicability for CE enantioseparations.