The macrocyclic glycopeptides, vancomycin, teicoplanin, and ristocetin A ar
e naturally occurring chiral molecules that have been developed into one of
the most useful classes of chiral stationary phases (CSPs) for HPLC, Since
these chiral selectors are structurally related, they tend to have similar
, but not identical, enantioselectivities for most compounds. CSPs, of this
type, with opposite enantioselectivities are rare. Two exceptions have bee
n found to this. The oxazolidiones (starting materials for asymmetric synth
esis) and dansyl amino acids all show a reversal in enantioselective retent
ion on one of these three related CSPs. By using the HPLC assays developed
for these compounds, the levels of enantiomeric impurities can be measured
down to similar to0.01%. The enantiomeric purity of commercial oxazolidione
s was determined.