Teichoic acid and lipoteichoic acid of <i>Streptococcus pneumoniae</i> possess identical chain structures

Fischer, Werner; Behr, Thomas M.; Hartmann, Rudolf; Peter‐Katalinić, Jasna; Egge, Heinz

doi:10.1111/j.1432-1033.1993.tb18102.x

Cited by 183 publications

(177 citation statements)

References 39 publications

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“…Two examples may illustrate this : pneumococcal teichoic acid has the capacity to activate the alternative complement pathway (Winkelstein and Tomasz, 1978). It possesses the same structure as the hydrophilic chain of lipoteichoic acid, but, not being amphiphilic, forms monomolecular solutions (Fischer et al, 1993). Micellar pneumococcal lipoteichoic acid lacks this activating capacity but can acquire it through binding to the surface of erythrocytes (Hummel et a]., 1985); this binding occurs through insertion of the acyl chains into the lipid bilayer and predictably results in an oriented presentation of single chains.…”

Section: Discussionmentioning

confidence: 99%

Small‐Angle X‐Ray Scattering Analysis of Pneumococcal Lipoteichoic Acid Phase Structure

Fischer

Markwitz

Labischinski

1997

European Journal of Biochemistry

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X-Ray-scattering analysis was performed on micelles of lipoteichoic acid from Streptococcus pneumoniae. This lipoteichoic acid differs from poly(g1ycerophosphate) and poly(glycosylg1ycerophosphate) lipoteichoic acids by a unique positively charged diacylglyceroglycolipid anchor and a complex structure of the hydrophilic chain which is composed of zwitterionic tetrasaccharide ribitol phosphate repeats each carrying two zwitterionic phosphocholine substituents. The size distribution of the lipoteichoic acid micelles was sufficiently homogenous to determine their size and some related molecular parameters by small-angle scattering analysis. Nearly independent on the ionic strength of the aqueous dispersion, an average micelle contained about 150 lipoteichoic acid molecules arranged in a spherical assembly with a diameter of about 23 nm, whereby the hydrophilic region occupied an outer shell of about 8.5 nm thick- A comparison with the micelle of poly(g1ycerophosphate) lipoteichoic acid of Staphylococcus aureus suggests that the supramolecular structure is largely independent of the structure of the hydrophilic chain and solely dictated by the small cross-sectional area of the diacylglycerol moiety common to all lipoteichoic acids and lipoglycans of gram-positive bacteria.Keywords : lipoteichoic acid ; small-angle X-ray scattering ; micelle ; Streptococcus pneumoniae.Lipoteichoic acids and lipoglycans are lipid macroamphiphiles in the cytoplasmic membrane of numerous gram-positive bacteria. Lipoteichoic acids occur in one subdivision in which the DNA contains less than 5 5 % guanine + cytosine, whereas lipoglycans preferentially appear associated with the other subdivision in which the guanine + cytosine content of DNA is higher than 55% (Fischer, 1990(Fischer, , 1994Sutcliffe, 1994). Most widespread is the classical type of lipoteichoic acid which possesses a single unbranched 1,3-linked poly(g1ycerophosphate) chain attached by a phosphodiester bond to a diacylglyceroglycolipid (Fig. 1). The glycerophosphate residues are at position 2 partially substituted with D-alanine ester and in certain lipoteichoic acids additionally with glycosyl residues. Poly(g1yco-sylglycerophosphate) lipoteichoic acids constitute a second less widespread type in which a monosaccharide or disaccharide is intercalated between the glycerophosphate residues (Koch and Fischer, 1978 ;Fischer, 1994). The largest modification of the basic structure shows the lipoteichoic acid of Streptococcus pneurnoniae (Behr et al., 1992). The glycerophosphate moieties are replaced by ribitol phosphate residues (Fig. 1). Intercalated between them is a tetrasaccharide which contains D-ghCOSe, the positively charged 2-acetamido-4-amino-2,4,6-trideoxy-~-galactose, and two N-acetyl-D-galactosaminy] residues each of which is substituted at 0 6 with a zwitterionic phosphocholine residue. Recently we studied the supramolecular structure of lipoteichoic acids in aqueous dispersion by X-ray diffraction analysis and found that variously substituted poly(g1ycerophospha...

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Section: Discussionmentioning

confidence: 99%

Small‐Angle X‐Ray Scattering Analysis of Pneumococcal Lipoteichoic Acid Phase Structure

Fischer

Markwitz

Labischinski

1997

European Journal of Biochemistry

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“…Phosphocholine has recently been reported to be a constituent of the glycosphingolipid of the annelid Pheretima hilgendorfi (15), of lipoteichoic acid (16), and of the cell wall associated teichoic acid of Streptococcus pneumoniae (17). In Haemophilus influen- Table I.…”

Section: Discussionmentioning

confidence: 99%

Primary Structure of a New Phosphocholine-containing Glycoglycerolipid of Mycoplasma fermentans

Zähringer

Wagner

Rietschel

et al. 1997

Journal of Biological Chemistry

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The human pathogen Mycoplasma fermentans PG18 was isolated from the urogenital tract several decades ago (1). Because of reports indicating its possible role as a cofactor accelerating the progression of human immunodeficiency virus disease, its significance as a pathogen in other immunocompromised patients (2), and its role in the pathogenesis of rheumatoid arthritis, interest in M. fermentans has recently increased (3). Although little is known of the molecular mechanisms underlying M. fermentans pathogenicity (4), it has been shown that human immunodeficiency virus-associated cytopathic effects could be increased by the presence of M. fermentans (2) and that M. fermentans is capable of fusing with T-cells and peripheral lymphocytes (5).It is reasonable to assume that Mycoplasma membrane components are involved in the attachment and fusion of the microbe with eukaryotic host cells. Salman et al. (6) isolated an unusual phospholipid from the cell membranes of M. fermentans and showed that this material (compound X) was capable of enhancing the fusion of small, unilamellar vesicles with MOLT-3 lymphocytes in a dose-dependent manner.Matsuda et al. (4) isolated two glycoglycerolipids (GGPL-I 1 and GGPL-III) from M. fermentans. GGPL-I structure was shown to be 6Ј-O-phosphocholine-␣-D-glucopyranosyl-1,2-diacyl-sn-glycerol (7) as elucidated by mass and NMR spectroscopy. It was later shown (4) that the structure of a more polar glycolipid (GGPL-III) isolated from the same strain of M. fermentans was very similar to that of GGPL-I. The chemical structure of GGPL-III, however, has so far remained obscure. The only distinguishing structural feature known is that it differs from GGPL-I in having an additional amino residue (4). Both GGPLs were shown to be species-specific major lipid antigens of M. fermentans (4).Here we describe the structural analysis of a new type of polar lipid isolated from M. fermentans, and we present the complete structural analysis of MfGL-II. 2 Furthermore, we show that both glycolipids of M. fermentans, GGPL-I and GGPL-III, share the basic structure of 6Ј-O-phospho-␣-D-glucopyranosyl-(1Ј33)-1,2-diacyl-glycerol (7) but differ in their polar head groups. MATERIALS AND METHODS Growth of the Organism-Cultures of M. fermentans strain PG18and strain Incognitus (provided by S.-C. Lo, Armed Forces Institute of Pathology, Washington, D.C.) were grown in a modified Channock medium (8) inoculated with a 48-h culture at an inoculum level of 2% and incubated statically at 37°C. After 68 h the cells were harvested, washed twice, and freeze-dried as described previously (8) with yields ranging from 130 to 160 mg dry weight per liter of medium.Lipid Extraction and Purification-Freeze-dried cells were suspended in 25 mM Tris/HCl, pH 7.5, containing 0.25 M NaCl to a final concentration of 25 mg of cells per ml. Lipids were extracted from cell suspensions by the method of Bligh and Dyer (9) and concentrated to near dryness on a rotary evaporator. Quantitative separation of MfGL-II was achieved by silica gel colu...

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“…The glycan strands of the parental strain were found to be partly Ndeacetylated as indicated by the incompleteness of the lysozyme digestion (Fig. 5): in addition to the expected main products, the reduced form of GlcNAcMurNAc and (GlcNAcMurNAc) 2 , additional peaks appeared in the elution profile between 30 and 50 min. After chemical N-acetylation in vitro these peaks became better resolved and shifted toward higher retention times, indicating that the peaks represented glycan fragments with different N-deacetylation patterns.…”

Section: Identification Of N-deacetylated Amino Sugars In the Pneu-mentioning

confidence: 99%

“…The resulting muropeptides were reduced with sodium borohydride and analyzed by reversed-phase HPLC according to Severin et al 2 using similar conditions as in a published method (21).…”

Section: Isolation Of Glycan Strands and Analysis Of Their Lysozymementioning

confidence: 99%

The pgdA Gene Encodes for a PeptidoglycanN-Acetylglucosamine Deacetylase in Streptococcus pneumoniae

Vollmer

Tomasz

2000

Journal of Biological Chemistry

228

125

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Analytical work on the fractionation of the glycan strands of Streptococcus pneumoniae cell wall has led to the observation that an unusually high proportion of hexosamine units (over 80% of the glucosamine and 10% of the muramic acid residues) was not N-acetylated, explaining the resistance of the peptidoglycan to the hydrolytic action of lysozyme, a muramidase that cleaves in the glycan backbone. A gene, pgdA, was identified as encoding for the peptidoglycan N-acetylglucosamine deacetylase A with amino acid sequence similarity to fungal chitin deacetylases and rhizobial NodB chitooligosaccharide deacetylases. Pneumococci in which pgdA was inactivated by insertion duplication mutagenesis produced fully N-acetylated glycan and became hypersensitive to exogenous lysozyme in the stationary phase of growth. The pgdA gene may contribute to pneumococcal virulence by providing protection against host lysozyme, which is known to accumulate in high concentrations at infection sites.The unusual complexity and diversity of the cell surface of Streptococcus pneumoniae is apparent both in the capsular structure and in the underlying cell wall structure of this bacterium, and this complexity and diversity may be related to the multiplicity of interactions of this microbe and its human host. S. pneumoniae is capable of producing at least 90 chemically distinct capsular polysaccharides (1). The cell wall of this microorganism contains a teichoic acid of unusually complex chemistry (2, 3) the components of which include ribitol phosphate, galactosamine, trideoxydiaminohexose, and covalently linked phosphocholine residues (4). The peptidoglycan of S. pneumoniae is also unusual because its stem peptides are cross-linked in both a direct and an indirect manner (5). Furthermore, the proportion of distinct linear and branched muropeptides in the peptidoglycan is clonally related (6). The pneumococcal cell wall is a potential target for components of the first line host defense such as lysozyme. In addition, the peptidoglycan and teichoic acid may represent bacterial ligands recognized by the innate immune system of the host.The recent introduction of high resolution analytical techniques and genetic approaches began to shed light on the determinants and biological functions of the pneumococcal cell wall. In this study we describe the identification of a genetic determinant, pgdA, of the first bacterial peptidoglycan GlcNAc deacetylase. We show that the innate activity of this enzyme is responsible for the high proportion of non-acetylated hexosamine residues in the peptidoglycan that appears to play a role in the resistance of S. pneumoniae to the activity of exogenous lysozyme, an enzyme that is known to accumulate in high concentrations at infection sites. EXPERIMENTAL PROCEDURESBacterial Strains, Plasmids, and Growth Media-Cultures of S. pneumoniae R36A, a non-encapsulated laboratory strain from the Rockefeller University collection, were grown in a casein-based semi-synthetic medium (C ϩ Y) containing 1 mg/ml yeast extract (7) o...

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Teichoic acid and lipoteichoic acid of Streptococcus pneumoniae possess identical chain structures

Cited by 183 publications

References 39 publications

Small‐Angle X‐Ray Scattering Analysis of Pneumococcal Lipoteichoic Acid Phase Structure

Small‐Angle X‐Ray Scattering Analysis of Pneumococcal Lipoteichoic Acid Phase Structure

Primary Structure of a New Phosphocholine-containing Glycoglycerolipid of Mycoplasma fermentans

The pgdA Gene Encodes for a PeptidoglycanN-Acetylglucosamine Deacetylase in Streptococcus pneumoniae

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