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

Pedersen, Christian Marcus; Figueroa-Perez, Ignacio; Ulmer, Artur J.; Zähringer, Ulrich; Schmidt, Richard R.

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

Files

Schmidt etal.pdf(5.97 MB)

Date

2012

Authors

Pedersen, Christian Marcus

Figueroa-Perez, Ignacio

Ulmer, Artur J.

Zähringer, Ulrich

Schmidt, Richard R.

Publication type

Journal article

Published in

Tetrahedron ; 68 (2012), 4. - pp. 1052-1061. - ISSN 0040-4020

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 (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).

Subject (DDC)

540 Chemistry

Keywords

Gram-positive bacteria,Glycosylation,Cytokines,Lipoteichoic acid,Carbohydrates

Cite This

ISO 690

PEDERSEN, 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. 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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