Lipopolysaccharide chemical structure

O. Holst and H. Brade, in D. C. Morrison and J. L. Ryan (Eds.), Bacterial Endotoxic Lipopolysaccharides Chemical Structure of the Core Region of Lipopolysaccharides, p. 135. CRC Press, Boca Raton, FL, 1992. 

The biomedical importance of infections by gram-negative pathogens and the consequences of septic shock have drawn much attention to lipid A, the toxic subcomponent of the lipopolysaccharide endotoxin of these organisms. A comprehensive account of the chemical structures and biological behavior of the lipid A structures is presented here by Zahrihnger, Lindner, and Rietschel. The chapter incorporates much of their own work from the... 

Figure 3.37. Structure of a generalized lipopolysaccharide (LPS) molecule. LPS consitutes the major structural component of the outer membrane of Gram-negative bacteria. Although LPS of different Gramnegative organisms differ in their chemical structure, each consists of a complex polysacharide component, linked to a lipid component. Refer to text for specific details...

Of the lipid portions of bacterial macromolecular amphiphi-les, that of lipopolysaccharides is the structurally most complex. For its designation the term lipid A has been coined. More specifically, it was suggested that the lipid, as it is present in intact lipopolysaccharide, should be called lipid A, while the lipid in a separated form should be termed free lipid A (10,11). This nomenclature will be used throughout this paper. In the following, ways and methods will be described which have been used to elucidate the chemical structure of lipid A. The present discussion will deal in more detail with the elucidation of the structure of Salmonella lipid A. Relative to this structure, chemical features of other lipid A s will then be discussed. 

Certain strains of cyanobacteria produce toxins. These cyanobacterial toxins can be classified according to their chemical structure or their toxicity. Table 16.1 summarises the characteristics of the main cyanobacterial toxins. Depending on the chemical structure, there are cyclic peptides, alkaloids and lipopolysaccharides. According to the toxic effects, they are classified as ... 

H. Brade Chlamydial lipopolysaccharide chemical and antigenic structure, biosynthesis, and medical applications... 

Heine, H., Muller-Loennies, S., Brade, L., Lindner, B., Brade, H. Endotoxic activity and chemical structure of lipopolysaccharides from Chlamydia trachomatis serotypes E and L2 and Chlamydophila psittaci 6BC. Eur J Biochem 270 (2003) 440-450. 

Holst, O. Chemical structure of the core region of lipopolysaccharides. an update. Trends Glycosci Glycotechnol 14 (2002) 87-103. 

Kaczynski, Z., Braun, S., Lindner, B., Niehaus, K., Holst, O. Investigation ofthe chemical structure and biological activity of oligosaccharides isolated from rough-type Xanthomonas campestris pv. campestris B100 lipopolysaccharides. J Endotoxin Res 13 (2007) 101-108. 

Rietschel, E.T., Brade, H., Brade, L., Brandenburg, K., Schade, U.F., Seydel, U., Z hringer U., Galanos, C., Ltideiitz, O., Westphal, O., Labischinski, H., Kusumoto, S., Shiba, T. Lipid A, the endotoxic center of bacterial lipopolysaccharides Relation of chemical structure to biological activity. Prog Clin Biol Res 231 (1987) 25-53. 

Zahringer, U., Knirel, Y.A., Lindner, B., Helbig, J.H., Sonnesson, A., Marre, R., Rietschel, E.T. The lipopolysaccharide of Legionella pneumophila serogroup I (strain Philadelphia 1) Chemical structure and biological significance. Prog Clin Biol Res 392 (1995) 113-139. 

Aspinall GO, McDonald AG, Raju TS, Pang H, Moran AP (1993) Chemical structures of the core regions of Campylobacter jejuni serotypes 0 1, 0 4, 0 23, and 0 36 lipopolysaccharides. Eur J Biochem 213 1017-1027. 

As reviewed by Rietschel Cavaillon (1-3), the term endotoxin was coined by Richard Pfeiffer, a student of Robert Koch. Pfeiffer first identified endotoxin as an agent responsible for fever and shock in animals that were injected with heat-killed preparations of Vibrio cholerae, or organisms that had been neutralized with antibodies (4). Until the end of his career, he was unaware that the O-antigens of gramnegative bacteria were covalently attached to the substance he had called endotoxin. It fell to Boivin, Staub, Luderitz, and others to demonstrate the lipopolysaccharide nature of endotoxin, to show that it was the principal glycolipid component of the outer membrane of gram-negative bacteria, and ultimately, to solve its chemical structure (5-8). 

G. O. Aspinall, A. G. McDonald, T. S. Raju, H. Pang, S. D. Mills, L. A. Kurjanczyk, and J. L. Penner, Serological diversity and chemical structures of Campylobacter jejuni low-molecular-weight lipopolysaccharides, J. Bacteriol., 174 (1992) 1324-1332. 

II. The Chemical Structure ot Helicobacter pylori Type Strain Lipopolysaccharide ... 

Tliis article focuses on the chemical structure, biosynthesis, and potential pathogenic role of the lipopolysaccharides (LPSs) from H. pylori. The structures of LPSs isolated from Helicobacter species found in nonhuman primates, which give rise to similar gastric symptoms in their respective hosts, are also described. LPSs are glycolipid structures carried by bacteria on their cell surfaces, which are actively involved in biochemical interactions between the bacterium and its host. ... 

IL The Chemical Structure of Helicobacter pylori Type Strain Lipopolysaccharide The Lewis X O-Chain... 

The chemical structure of lipid A of lipopolysaccharide isolated from Comamonas testosteroni was recently determined by lida et al. (1996) by means of methylation analysis, mass spectrometry and NMR. The lipid A backbone was found to consist of 6-0-(2-deoxy-2-amino-P-D-glucopyrano-syl)-2-deoxy-2-amino-alpha-D-glucose which was phosphorylated in positions 1 and 4. Hydroxyl groups at positions 4 and 6 were unsubstituted, and position 6 of the reducing terminal residue was identified as the attachment site of the polysaccharide group. Fatty acid distribution analysis and ES/MS of lipid A showed that positions 2,2, 3 and 3 of the sugar backbone were N-acylated or O-acylated by R-3-hydroxydecanoic acid and that the hydroxyl groups of the amide-linked residues attached to positions 2 and 2 were further O-acylated by tetradecanoic and dodecanoic acids, respectively. 

In the last decades, structural details of lipopolysaccharides derived from selected bacterial serotypes have been elucidated, and it became possible to ascribe distinct biological properties to distinct domains of the macromolecule. As a consequence, a number of organic chemists have undertaken the chemical synthesis of biologically relevant partial structures of lipopolysaccharide. 

Galanos, C., Luderitz, O., Kusumoto, S., and Shiba, T. (1983). The chemistry of bacterial lipopolysaccharides with emphasis on the structure and chemical synthesis of their lipid A component. In Handbook of Natural Toxins, Vol II, Bacterial Toxins (Tu, Habig and Hardegree, eds.) Marcel Dekker, Inc., New York. 

Amano, K.I., Williams, J.C., Dasch, G.A. Structural properties of lipopolysaccharides from Rickettsia typhi and Rickettsia prowazekii and their chemical similarity to the lipopolysac-charide from Proteus vulgaris 0X19 used in the Weil-Felix test. Infect Immun 66 (1998) 923-926. 

Rosner, M.R., Tang, J., Barzilay, I., Khorana, H.G. Structure of the lipopolysaccharide from an Escherichia coli heptose-less mutant. I. Chemical degradations and identification of products. J Biol Chem 254 (1979) 5906-5917. 

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