Peptidoglycan acids

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

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. 

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

Paper ionophoresis, sugars, Maurice Stacey s work, 17 Pectic acid, 350, 352,414 Pectin, 348, 350-353 Pectinic acid, 353 Pentulose, synthesis, 281 D-cryt/iro-Pentulose 5-phosphate, 289 Peptidoglycans, 167-168 Per-O-acetylated di-D-fructose dianhydride derivatives... 

The first known 1-carboxyethyl ether of a sugar was 2-amino-3-0-[(/ )-l-carboxyethyl]-2-deoxy-D-glucose or muramic acid (37). It is a component of the polysaccharide moiety of the peptidoglycan in the bacterial cell-wall. It is partially replaced by the mamo isomer, 2-amino-3-6>-[(/ )-l-carboxy-ethyl]-2-deoxy-D-mannose, in the peptidoglycan from Micrococcus lyso-deikticus. 

In the peptidoglycan from some mycobacteria, the muramic acid is A -gly-colylated, not A-acetylated. As already mentioned, ester-linked lactic acid... 

Fig. 1.2 A, peptidoglycan of Escherichia coli. , A -acetylmuramic acid , Af-acetylglucosamine. B, repeating unit of peptidoglycan ofE. coli. L-ala, L-alanine D-glu, D-glutamine DAP, diaminopimelic acid D-aia, D-alanine.

Bacterial cell wall j3-Lactams Glyoopeptides Cycloserine Isoniazid Ethambutol Inhibit peptidoglycan synthesis Inhibit peptidoglycan synthesis Inhibits peptidoglycan synthesis Inhibits mycolic acid synthesis Inhibits arabinogalactan synthesis None in mammalian cells None in mammalian cells None in mammalian cells None in mammalian cells None in mammalian cells... 

Fig. 8.1 Biosynthesis of peptidoglycan. The large circles represent A -acetylglucosamine orN-acetylmuramic acid to the latter is linked initially a pentapeptide chain comprising L-alanine, D-glutamic acid and meso-diaminopiraelic acid (small circles) terminating in two D-alanine residues (small, darker circles). The lipid molecule is undecaprenyl phosphate. In the initial (cytoplasm) stage where inhibition by the antibiotic D-cycloserine is shown, two molecules of Dalanine (small circles) are converted by an isomerase to the D-forms (small, darker circles), alter which a ligase joins the two D-alanines together to produce a D-alanyl-D-alanine dipeptide.

The cell walls of mycobacteria contain three structures peptidoglycan, an arabinogalactan polysaccharide and long chain hydroxy fatty acids (mycolic acids) which are all covalently linked. Additional non-covalently attached lipid components found in the wall include glycolipids, various phospholipids and waxes. The lipid-rich nature of the mycobacterial wall is responsible for the characteristic acid-fastness on staining and serves as a penetration barrier to many antibiotics. Isoniazid and ethambutol have long been known as specific antimycobacterial agents but their mechanisms of action have only recently become more clearly understood. 

A. Fox and R. M. T. Rosario, Quantification of muramic acid, a marker for bacterial peptidoglycan in dust collected from hospital and home air-conditioning filters using gas-chromatography mass spectrometry. Indoor Air-Intemat. J. Air Quality Cl. 4 239 (1994). 

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