Vancomycin amino acids enantiomers recognition

Recently, CSPs based on macrocyclic antibiotics such as vancomycin, teicoplanin, or ristocetin A have been introduced. These CSPs can separate many enantiomers of underivatized and derivatized amino acids in the normal and reversed-phase modes. In addition to n-n interactions, hydrogen bonding, electrostatic and hydrophobic (in the case of reversed-phase mode) interactions could help in the chiral recognition of amino acid derivatives. 

Commercially available silica gel plates coated with acid or basic chiral selectors [o-galacturonic acid, l-(- -)-tartaric acid, L-lactic acid, (-)-brucine] were used for the separation of racemic ephedrine, atropine, neutral amino acids, and their 3-phenyl-2-thiohydantoins (PTH) derivatives. The use of amino acids as chiral selectors involved further possibilities of enantiomer separation owing to the simultaneous presence of basic and acidic groups. In fact, L-aspartic acid, L-lysine, L-histidine, L-arginine, and L-ser-ine resolved racemic alkaloids, (3-blockers, profens, some amino acids, and their Dns derivatives. Macrocyclic antibiotics [i.e., (-)-erythromycin and (-)-vancomycin] were also used as chiral agents for the separation of enantiomeric DNs amino acids. The mechanisms of chiral recognition was investigated by Aboul-Enein, El-Awady, and Heard they hypothesized that the formation of... 

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