Glycopeptides teicoplanin

Another macrolytic glycopeptide used in chiral chromatography is the amphoteric glycopeptide Teicoplanin which is commercially available under the trade name of CH OBIOTIC T. 

The macrocyclic glycopeptide Teicoplanin has been used very successfully by Irv Wainer and his group at Georgetown University, to monitor the enantiomers of Albuterol in blood plasma. Albuterol (supplied under the names of Proventil and Ventolin) is used to dilate breathing passages and make breathing easier. It is often used to prevent bronchospasm in certain cases of lung diseases. 

Astec) amphoteric glycopeptide, Teicoplanin polar organic N-derivatized amino acids, that is, FMOC, CBZ, and hydroxy-carboxylic acids, acidic compounds including carboxylic acids and phenols, small peptides, neutral aromatic analytes and cyclic aromatic and aliphatic amines... 

Astec) glycopeptide, Teicoplanin improvements for preparative separations ionic ... 

Fig. 2-1 Proposed structures of three macrocycUc glycopeptides. On teicoplanin, R = 8-methyl-nonanoic acid.

Macrocyclic glycopeptides. The first of these CSPs - based on the cavity of the antibiotic vancomycin bound to silica - was introduced by Armstrong [25]. Two more polycyclic antibiotics teicoplanin and ristocetin A, were also demonstrated later. These selectors are quite rugged and operate adequately in both normal-phase and reversed-phase chromatographic modes. However, only a limited number of such selectors is available, and their cost is rather high. 

Acquired resistance to the glycopeptides is transposon-mediated and has so far been largely confined to the enterococci. This has been a problem clinically because many of these strains have been resistant to all other antibiotics and were thus effectively untreatable. Fortunately, the enterococci are not particularly pathogenic and infections have been confined largely to seriously ill, long-term hospital patients. Two types of acquired glycopeptide resistance have been described (Woodford et al. 1995). The VanA phenotype is resistant to vancomycin and teicoplanin, whereas VanB is resistant... 

Fig. 9.4 Organization of glycopeptide-resistance genes in transposon Tnl546. IR, invested repeats HPK, histidine protein kinase TcR, low level teicoplanin resistance.

Fig. 2-5. Examples showing the complementary separations on glycopeptide CSPs. (A) Separation of N-CBZ-norvaline on vancomycin (left) and teicoplanin (right). The mobile phase was methanol 1 % triethylammonium acetate (20/80 v/v) pH 4.1. (B) Separation of warfarin on teicoplanin (left) and vancomycin (right) CSPs. The mobile phase was acetonitrile 1 % triethylammonium acetate (10/90 v/v) pH 4.1. (C) Separation of naproxen on teicoplanin (left) and ristocetin A (right). The mobile phase was methanol 0.1 % triethylammonium acetate (30/70 v/v) pH 4.1. All columns were 250 x 4.6 mm i.d. The flow rate for all the separations was 1 mL min1 at ambient temperature (23 °C).

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