Glycopeptides synthesis and antibacterial activity

The glycopeptides vancomycin and teicoplanin are complex heterocyclic molecules consisting of a multi-peptide backbone to which are attached various substituted sugars. These compounds bind to acyl-D-alanyl-D-alanine in peptidoglycan, thereby preventing the addition of new building blocks to the growing cell wall (Figure 1).

Figure 1. Binding site of glycopeptides to peptidoglycan.

Glycopeptides do not penetrate the external membrane of Gram-negative bacteria, so their spectrum of activity is limited to Gram-positive organisms. Acquired resistance is growing with enterococci and C. difficile being now widely prevalent and staphylococci exhibiting reduced susceptibility. Avoparcin, a glycopeptide formerly used in animal husbandry has been implicated in promoting resistance in enterococci, but human use of glycopeptides is equally important. Some Gram-positive genera, including Lactobacillus spp., Pediococcus spp., and Leuconostoc spp. are inherently resistant to glycopeptides, but fortunately these organisms are seldom implicated in disease.

Mechanism of Action


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