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J. Biol. Chem., Vol. 281, Issue 45, 33849-33859, November 10, 2006

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Comparison of Lipoteichoic Acid from Different Serotypes of Streptococcus pneumoniae^*

Christian Draing¹, Markus Pfitzenmaier¹, Sebastiana Zummo^¶, Giuseppe Mancuso^¶, Armin Geyer, Thomas Hartung^||, and Sonja von Aulock²

From the Department of Biochemical Pharmacology, University of Konstanz, P. O. Box M668, 78457 Konstanz, Germany, the Department of Organic Chemistry, University of Marburg, 35043 Marburg, Germany, the Department of ^¶Pathology and Experimental Microbiology, University of Messina, 98125 Messina, Italy, and the ^||European Centre for the Validation of Alternative Methods, Joint Research Centre, 21020 Ispra, Italy

Pneumococcal lipoteichoic acid (LTA) is known to have a completely different chemical structure compared with that of Staphylococcus aureus: the polyglycerophosphate in the backbone is replaced in the pneumococcal LTA by a pentamer repeating unit consisting of one ribitol and a tetrasaccharide carrying the unusual substituents phosphocholine and N-acetyl-D-galactosamine. Neither D-alanine nor N-acetyl-D-glucosamine, which play central roles in the biological activity of the staphylococcal LTA, has been reported. The extraction using butanol is more gentle compared with the previously reported chloroform-methanol extraction and results in a higher yield of LTA. We characterized the LTA of two different strains of Streptococcus pneumoniae:R6 (serotype 2) and Fp23 (serotype 4). NMR analysis confirmed the structure of LTA from R6 but showed that its ribitol carries an N-acetyl-D-galactosamine substituent. The NMR data for the LTA from Fp23 indicate that this LTA additionally contains ribitol-bound D-alanine. Dose-response curves of the two pneumococcal LTAs in human whole blood revealed that LTA from Fp23 was significantly more potent than LTA from R6 with regard to the induction of all cytokines measured (tumor necrosis factor, interleukin-1 (IL-1), IL-8, IL-10, granulocyte colony-stimulating factor, and interferon ). However, other characteristics, such as lack of inhibition by endotoxin-specific LAL-F, Toll-like receptor 2 and not 4 dependence, and lack of stimulation of neutrophilic granulocytes, were shared by both LTAs. This is the first report of a difference in the structure of LTA between two pneumococcal serotypes resulting in different immunostimulatory potencies.

Received for publication, March 22, 2006 , and in revised form, August 29, 2006.

^* This study was supported by the German Research Council (FOR 434). The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

¹ These authors contributed equally to this work.

² To whom correspondence should be addressed. Tel.: 49-7531-88-2121; Fax: 49-7531-88-4156; E-mail: Sonja.v-aulock{at}uni-konstanz.de.

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