Synthesis of the repeating unit of the lipoteichoic acid of Streptococcus pneumoniae |
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| Authors: | Christian Marcus Pedersen Ignacio Figueroa-Perez Artur J Ulmer Ulrich Zähringer Richard R Schmidt |
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| Institution: | 1. Universität Konstanz, Fachbereich Chemie, Fach 725, D-78457 Konstanz, Germany;2. Forschungszentrum Borstel, Leibniz-Zentrum für Medizin und Biowissenschaften, Parkallee 1-40, D-23845 Borstel, Germany;3. Chemistry Department—Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia;4. Department of Chemistry, University of Copenhagen, Universitetsparken 5, 2100 Copenhagen, Denmark |
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| Abstract: | The lipoteichoic acid repeating unit of Streptococcus pneumoniae is a complex pseudopentasaccharide (3). It consists of one ribitol-phosphate, one 2-acetamino-4-amino-2,4,6-trideoxy-galactose, one glucose and two galactosamine residues each differently linked, but both carrying one phosphocholine substituent, at position 6. Suitable building blocks (6–10) for efficient and diastereocontrolled ligations were designed, thus providing, after complete deprotection, the target molecule in high purity. Biological tests revealed that repeating unit 3, lacking the lipid moiety, did not stimulate a pro-inflammatory response in human monocytes (hMNCs). |
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