Synthesis of the core structure of the lipoteichoic acid of streptococcus pneumoniae

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2010
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Pedersen, Christian Marcus
Figueroa-Perez, Ignacio
Boruwa, Joshodeep
Lindner, Buko
Ulmer, Artur J.
Zähringer, Ulrich
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Streptococcus pneumoniae LTA is a highly complex glycophospholipid that consists of nine carbohydrate residues: three glucose, two galactosamine and two 2-acetamino-4-amino-2,4,6-trideoxygalactose (AATDgal) residues that are each differently linked, one ribitol and one diacylated glycerol (DAG) residue. Suitable building blocks for the glucose and the AATDgal residues were designed and their synthesis is described in this paper. These building blocks permitted the successful synthesis of the core structure GlcBeta(1-3)AATDgalBeta(1-3)GlcAlpha(1-O)DAG in a suitably protected form for further chain extension (lb, le) and as unprotected glycolipid (la) that was employed in biological studies. These studies revealed that la as well as 1 lead to interleukin-8 release, however not via TLR2 or TLR4 as receptor.

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540 Chemie
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carbohydrates, glycolipids, glycosidation, receptor recognition, total synthesis
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ISO 690PEDERSEN, Christian Marcus, Ignacio FIGUEROA-PEREZ, Joshodeep BORUWA, Buko LINDNER, Artur J. ULMER, Ulrich ZÄHRINGER, Richard R. SCHMIDT, 2010. Synthesis of the core structure of the lipoteichoic acid of streptococcus pneumoniae. In: Chemistry - A European Journal. 2010, 16(42), pp. 12627-12641. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201001204
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@article{Pedersen2010-11-08Synth-384,
  year={2010},
  doi={10.1002/chem.201001204},
  title={Synthesis of the core structure of the lipoteichoic acid of streptococcus pneumoniae},
  number={42},
  volume={16},
  issn={0947-6539},
  journal={Chemistry - A European Journal},
  pages={12627--12641},
  author={Pedersen, Christian Marcus and Figueroa-Perez, Ignacio and Boruwa, Joshodeep and Lindner, Buko and Ulmer, Artur J. and Zähringer, Ulrich and Schmidt, Richard R.}
}
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