A covalently bonded teicoplanin chiral stationary phase for HPLC enantioseparations

Abstract

A macrocyclic glycopeptide antibiotic containing a hydrophobic "tail" is covalently attached to silica gel via linkage chains. This material is extensively evaluated as a chiral stationary phase (CSP) for HPLC. The relevant structural features of the teicoplanin molecule which make it an effective chiral selector are discussed. The teicoplanin CSP appears to have excellent enantioselectivity for native amino acids, peptides, a-hydroxycarboxylic acids, and a variety of neutral analytes including cyclic amides and amines. Enantioseparations can be achieved in the reversed phase, normal phase, and "polar-organic" modes. This chiral selector is stable and the integrity of the CSP is excellent in all separation modes. Hence it can be considered a highly effective multimodal column. Optimization of these separations is discussed in terms of both selectivity and efficiency. Results indicate that the surface loading of the chiral selector affects all relevant separation parameters. A hypothesis is proposed to explain the enhanced efficiency obtained when using teicoplanin CSPs with higher surface coverage. It appears that teicoplanin is a widely applicable, highly effective chiral selector for HPLC enantioseparations.o 1995 Wiey-Liss, h c .

Chiral separation by chromatographic and electromigration techniques. A Review

“…Macrocyclic antibiotics have been shown to be very effective chiral selectors both for HPLC and CE. The glycopeptides vancomycin [131], teicoplanin [132], ristocetin A [133] and avoparcin [134] as well as the polypeptide thiostrepton [131] and the ansamycin rifamycin B [131] have been used for the preparation of chiral HPLC phases. A comprehensive review on the application of macrocyclic antibiotics as chiral selectors for both HPLC and CE was recently given by Ward and Fattis [135].…”

“…A CSP based on vancomycin derivatized with 3,5-dimethylphenylisocyanate [131] showed different chiral recognition ability and resolved for example hydroxyzine and althiazide. Teicoplanin [132] was used for the separation of amino acids, dipeptides [140,141] and unusual aromatic balkyl amino acids [141]. Ristocetin A was shown to be applicable to a broad spectrum of compounds [133] using either normal-phase, polar organic or reversed-phase mode.…”

HPLC separation of amino acid enantiomers and small peptides on macrocyclic antibiotic‐based chiral stationary phases: A review

“…This is produced by Actinoplanes teichomyceticus and is active against aerobic and anaerobic Gram-positive bacteria both in vitro and in vivo [18,35]. The aglycone consists of four fused macrocyclic rings which form a "semirigid basket" (Fig.…”

“…The best enantioseparation was achieved with the Dns derivatives. One year later, Armstrong et al [18] introduced the T-A 2-2 selector, on which excellent enantioseparation was achieved for a variety of N-blocked protein amino acids in RP mode and POM, but the enantiomers of N-formylor N-acetyl-blocked amino acids were separable only in the case of aromatic amino acids. Fourteen N-Dns-protected protein amino acid enantiomers were separated on both T-A 22 , whereas no separation was observed on vancomycin.…”

Enantioselective liquid chromatography–mass spectrometry assay for the determination of ifosfamide and identification of the N-dechloroethylated metabolites of ifosfamide in human plasma

“…One of the advantages of the Chirabiotic T CSP is that it has been shown to achieve enantioselective separations in reversed phase, normal phase and polar organic modes [29]. Because of the hydrophilic nature of the analytes and the desire to have a mobile phase that was compatible with mass spectrometric detection, the polar organic mode was investigated and the effects on retention and enantioselectivity of phases composed of methanol, ethanol, 2-propanol and acetonitrile were examined, Table 1.…”