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The macrocyclic glycopeptides, vancomycin, teicoplanin, and ristocedn A are 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 been found to this. The oxazoHdiones (starting materials for asymmetric synthesis) and dansyl amino acids all show a reversal in enantioselective retention 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 ^0.01%. The enantiomeric purity of commercial oxazoHdiones was determined. Introduction The aglycone portion of all the macrocyclic glycopeptides contain either three or four fused macrocyclic rings (Figure 1). Together, these fused rings form a semirigid basket-

Unusual separations with macrocyclic glycopeptide chiral stationary phases and chromatographic analysis and characterization of microbes