Peptidoglycan

D,D-endopeptidase acting on maturing peptidoglycan D, D - c arb o xyp ep tidase transpeptidation is absent none apparent... 

Glycoconjugates. Another class of carbohydrates are the glycoconjugates (14), composed of glycoproteins, proteoglycans, peptidoglycans, and glycohpids. 

IV-Acetylglucosamine and IV-Acetylmuraniic acid Sugar derivatives in the peptidoglycan layer of bacterial cell walls. 

Cell wall Peptidoglycan a rigid framework of polysaccharide cross-linked by short peptide chains. Some bacteria possess a lipopolysaccharide- and protein-rich outer membrane. Mechanical support, shape, and protection against swelling in hypotonic media. The cell wall is a porous nonselective barrier that allows most small molecules to pass. 

FIGURE 8.18 Dolichol phosphate is an initiation point for the synthesis of carbohydrate polymers in animals. The analogous alcohol in bacterial systems, undecaprenol, also known as bactoprenol, consists of 11 isoprene units. Undecaprenyl phosphate delivers sugars from the cytoplasm for the synthesis of cell wall components such as peptidoglycans, lipopolysaccharides, and glycoproteins. Polyprenyl compounds also serve as the side chains of vitamin K, the ubiquinones, plastoquinones, and tocopherols (such as vitamin E). 

FIGURE 9.25 Teichoic acids are covalently linked to the peptidoglycan of Grampositive bacteria. These polymers of (a, b) glycerol phosphate or (c) ribitol phosphate are linked by phosphodiester bonds. 

Several drugs in current medical use are mechanism-based enzyme inactivators. Eor example, the antibiotic penicillin exerts its effects by covalently reacting with an essential serine residue in the active site of glycoprotein peptidase, an enzyme that acts to cross-link the peptidoglycan chains during synthesis of bacterial cell walls (Eigure 14.17). Once cell wall synthesis is blocked, the bacterial cells are very susceptible to rupture by osmotic lysis, and bacterial growth is halted. 

Fosfomycin is an antibiotic produced by several Streptomyces species [95, 96] as well as by the Gram-negative Pseudomonas syringiae and Pseudomonas viridiflava. dl, 98] As an analogue of phosphoenolpyruvate, it irreversibly inhibits UDP-N-acetylglu-cosamine-3-O-enolpymvyltransferase (MurA), the enzyme that catalyzes the first step in peptidoglycan biosynthesis [99]. 

Figure 6.7 Formation of cross-linkage between individual peptide chains in the peptidoglycan layer of S. aureus.

Many different types of carbohydrate-containing molecules are located on the surface of microbial cells. Some of these are components of die microbial cell wall and are limited to certain types of micro-organisms such as bacterial peptidoglycan, lipopolysaccharides, techoic adds and yeast mannans. Other polysaccharides are not... 

Penicillin has an interesting mode of action it prevents the cross-linking of small peptide chains in peptidoglycan, the main cell wall polymer of bacteria. Pre-existing cells are unaffected, but all newly produced cells are abnormally grown. The newborn cells are unable to maintain their wall rigidity, and they are susceptible to osmotic lysis. 

Gram-positive (whole organisms peptidoglycans [e.g., muramyl dipeptide] lipoteichoic acids exotoxins enterotoxins erythrogenic toxins group B polysaccharides)... 

Gram-negative (whole organisms peptidoglycans lipopolysaccharides [lipid A])... 

Lactam antibiotics are bicyclic or monocyclic azetidinone ring-containing compounds (Fig. 1). They kill bacteria by preventing the assembly of (4-3) peptidoglycans. These covalently closed net-like polymers form the matrix of the cell wall by which the bacteria can divide and multiply, despite their high internal osmotic pressure. 

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