Macrocyclic Antibiotics as a New Class of Chiral Selectors for Liquid Chromatography

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].…”

“…Hydrophobic parts of the analyte may be included into the hydrophobic basket and hydrogen bonds with the pendant arms as well as dipole stacking, ionic-, p-p interactions and steric repulsions are assumed to be the main interactions responsible for chiral recognition. Vancomycin [131] found application among others to the chiral separation of barbiturates, hydantoins, piperidine-2,6-dione and cyclic amides [136], dihydropyrimidinones [137], pyridone derivatives [138] and semi-synthetic ergot alkaloids [139]. A CSP based on vancomycin derivatized with 3,5-dimethylphenylisocyanate [131] showed different chiral recognition ability and resolved for example hydroxyzine and althiazide.…”

“…Vancomycin [131] found application among others to the chiral separation of barbiturates, hydantoins, piperidine-2,6-dione and cyclic amides [136], dihydropyrimidinones [137], pyridone derivatives [138] and semi-synthetic ergot alkaloids [139]. 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].…”

Chiral Separation of α-hydroxy Acids by Capillary Electrochromatography Using the Cathodic Detergent CTAB as Mobile Phase Additive to Speed up Analysis Time

“…Good chiral separations of α-hydroxy acids were shown by using L-4-hydroxyproline 11 bonded to 3 µm silica material in ligand-exchange CEC and by using the macrocyclic antibiotics Ristocetin A and teicoplanin aglycone (TAG) bonded to 3 µm silica material. 16 Macrocyclic antibiotics of the glycopeptide type were first introduced by Armstrong et al 17 and are nowadays wide spread chiral selectors in HPLC, CE and CEC.…”

Avaliação de fungos na obtenção do metabólito quiral e ativo fexofenadina

“…Introduzidas por ARMSTRONG et al (1994), as FEQs derivadas de antibióticos macrocíclicos são sintetizadas pela imobilização covalente de glicopeptídeos macrocíclicos como a vancomicina, rifamicina B, teicoplanina, tiostreptona, ristocetina A e outros a um suporte de sílica (LOURENÇO et al, 2010;BOCATO, 2012).…”