Enantioseparation of dipeptides and tripeptides by micro-HPLC comparing teicoplanin and teicoplanin aglycone as chiral selectors.

Martin G Schmid, Maria Hölbling, Nikola Schnedlitz, Gerald Gübitz

Index: J. Biochem. Biophys. Methods 61 , 1-10, (2004)

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Abstract

Chiral separation of glycyl- and diastereomeric dipeptides and tripeptides was performed by micro-HPLC using macrocyclic antibiotics as chiral selectors. Teicoplanin was compared with teicoplanin aglycone (TAG) regarding selectivity, efficiency and separation time. The stationary phases are based on teicoplanin and TAG chemically bonded to 3.5 mum silica gel. The material was packed into 10 cm x 1 mm stainless steel microcolumns. Different mobile phases were checked using the reversed phase mode. Both teicoplanin and TAG were found to show good chiral separation ability for dipeptides. Glycyl-dipeptides were baseline resolved and most of the diastereomeric dipeptides and tripeptides were separated into their four isomers. In this study, teicoplanin was found to be advantageous compared to TAG regarding separation time, although TAG showed the higher resolution power. Baseline resolution for some glycyl-dipeptides was obtained within 3 min, diastereomeric dipeptides were resolved in 7 min. This method was also shown to be applicable for enantiomer purity control.