Synthesis of the repeating unit of the lipoteichoic acid of streptococcus pneumoniae

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2012
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Pedersen, Christian Marcus
Figueroa-Perez, Ignacio
Ulmer, Artur J.
Zähringer, Ulrich
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Tetrahedron. 2012, 68(4), pp. 1052-1061. ISSN 0040-4020. Available under: doi: 10.1016/j.tet.2011.11.088
Zusammenfassung

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 (6e10) 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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Fachgebiet (DDC)
540 Chemie
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Gram-positive bacteria, Glycosylation, Cytokines, Lipoteichoic acid, Carbohydrates
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ISO 690PEDERSEN, Christian Marcus, Ignacio FIGUEROA-PEREZ, Artur J. ULMER, Ulrich ZÄHRINGER, Richard R. SCHMIDT, 2012. Synthesis of the repeating unit of the lipoteichoic acid of streptococcus pneumoniae. In: Tetrahedron. 2012, 68(4), pp. 1052-1061. ISSN 0040-4020. Available under: doi: 10.1016/j.tet.2011.11.088
BibTex
@article{Pedersen2012Synth-18127,
  year={2012},
  doi={10.1016/j.tet.2011.11.088},
  title={Synthesis of the repeating unit of the lipoteichoic acid of streptococcus pneumoniae},
  number={4},
  volume={68},
  issn={0040-4020},
  journal={Tetrahedron},
  pages={1052--1061},
  author={Pedersen, Christian Marcus and Figueroa-Perez, Ignacio and Ulmer, Artur J. and Zähringer, Ulrich and Schmidt, Richard R.}
}
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