For this study, we used the macrocyclic antibiotic teicoplanin, a molecule consisting of an aglycone peptide "basket" with three attached carbohydrate (sugar) moieties. The sugar units were removed and the aglycone was purified. Two chiral stationary phases (CSPs) were prepared in a similar way, one with the native teicoplanin molecule and the other with the aglycone. Twenty-six compounds were evaluated on the two CSPs with seven RPLC mobile phases and two polar organic mobile phases. The compounds were 13 amino acids or structurally related compounds (including DOPA, folinic acid, etc.) and 13 other compounds (such as carnitine, bromacil, etc.). The chromatographic results are given as the retention, selectivity, and resolution factors along with the peak efficiency and the enantioselective free energy difference corresponding to the separation of the two enantiomers. The polarities of the two CSPs are similar. It is clearly established that the aglycone is responsible for the enantioseparation of amino acids. The difference in enantioselective free energy between the aglycone CSP and the teicoplanin CSP was between 0.3 and 1 kcal/mol for amino acid enantioseparations. This produced resolution factors 2-5 times higher with the aglycone CSP. Four non amino acid compounds were separated only on the teicoplanin CSP. Six and five compounds were better separated on the teicoplanin and aglycone CSPs, respectively. Although the sugar units decrease the resolution of alpha-amino acid enantiomers, they can contribute significantly to the resolution of a number of non amino acid enantiomeric pairs.

Recent advances in high efficiency separation methods of bacteria allow their rapid identification and quantitation in some cases. A specific capillary electrophoresis (CE) technique is used to identify and quantitate Lactobacillus acidophilus in both pill and syrup health products as well as Bifidobacterium infantis in a powdered formula supplement. Cell viability can be evaluated as well. In some cases, both the living and dead bacterial cells as well as the molecular excipients can be evaluated in a single run.

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Avoparcin is a macrocyclic glycopeptide antibiotic structurally related to vancomycin, teicoplanin, and ristocetin A. When attached to 5‐μm spherical silica gel, the avoparcin proved to be an effective chiral stationary phase (CSP) that could be used in the reversed‐phase, normal‐phase, and polar‐organic modes. The avoparcin CSP was complimentary to the other macrocyclic glycopeptide CSPs in that it could resolve some racemates that the others could not, and vice versa. Some important compounds resolved on the avoparcin CSP include verapamil, thyroxine, mephenytoin, and 2‐imidazolidone‐4‐carboxylic acid. The use of this CSP and the optimization of separations on it are discussed. Avoparcin appears to be a useful addition to this family of CSPs. Chirality 10:627–660, 1998. © 1998 Wiley‐Liss, Inc.

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