Glycopeptide antibiotics chemical structure

Vancomycin Vancomycin (32.7.2) was isolated in 1956 from the products of the functional activity of actinomycetes Streptomyces orientalis (cnrrently Nocardia orientalis). Based on its chemical structure and contents, vancomycin is classified as a glycopeptide antibiotic. Its molecular mass is significantly more than practically any other used antibiotics [325-330]. 

Wolter F, Schoof S, Sussmuth R (2007) Synopsis of structural, biosynthetic, and chemical aspects of glycopeptide antibiotics. Top Curr Chem 267 143-185... 

Figure 1.3 Chemical structures of glycopeptides antibiotics vancomycin (1) [1], eremomycin (2) [15a], ristocetin A (3) [15b], and teicoplanin (4) [15c],...

Other complex glycopeptide antibiotics (90-96) produced by S. virginiae [83] contain galactose in their chemical structure. 

Further antibiotics, mainly derived from actinomycetes, are used for special applications in human and veterinary medicine [20]. These compounds have numerous chemical structures. The macrolides, tetracyclines, aminoglycosides, glycopeptides, and ansamycins for instance are used in antibacterial treatment whereas the anthracyclines reached the market to supplement anticancer chemotherapy. The fairly toxic polyether-type antibiotics are preferably used as anticoccidial agents. Due to the dramatically increasing resistance of clinical important bacterial strains new targets for the discovery of novel types of antibacterial agents are urgently needed. 

Fig. 7.15 Chemical structures of the glycopeptide-type antibiotics vancomycin, teicoplanin and ristocetin A. For teicoplanin the prevalent derivative (A2-2, 85%) of the teicoplanin complex is shown.

Nowadays, antibiotics are primarily classified according to the mechanism of their action, with similarity of chemical structure as a secondary factor. Penicillin and its derivatives inhibit the formation of bacterial cell walls (Fig. 3.38). Cephalosporins have the same active mechanism. Other compounds are taken up into bacterial DNA to form unstable molecules (quinolones, metronidazole) or inhibit peptide synthesis (tetracychnes, aminoglycosides, macrolides). Some antibiotics (e.g. glycopeptides) exert a complex effect. 

Figure 4.16 Chemical structures of the macrocyclic glycopeptide antibiotics (a) vancomycin, (b) teicoplanin, (c) avoparcin, (d) ristocetin A, that have been used as chiral selectors in CSPs for HPLC. Reproduced from Ward and Farris, J. Chromatogr. A 906 (2001), copyright (2001), with permission from Elsevier.

Wolter F, School S, Siissmuth RD (2007) Synopsis of Structural, Biosynthetic, and Chemical Aspects of Glycopeptide Antibiotics. 267 143-185 Woltinger J, see Greiner L (2007) 276 111-124... 

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