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

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

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

Files

Schmidt_etal.pdf(1.04 MB)

Date

2010

Authors

Pedersen, Christian Marcus

Figueroa-Perez, Ignacio

Boruwa, Joshodeep

Lindner, Buko

Ulmer, Artur J.

Zähringer, Ulrich

Schmidt, Richard R.

Publication type

Journal article

Published in

Chemistry - A European Journal ; 16 (2010), 42. - pp. 12627-12641. - ISSN 0947-6539. - eISSN 1521-3765

Abstract

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.

Subject (DDC)

540 Chemistry

Keywords

carbohydrates,glycolipids,glycosidation,receptor recognition,total synthesis

Cite This

ISO 690

PEDERSEN, 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. 16(42), pp. 12627-12641. ISSN 0947-6539. eISSN 1521-3765. Available under: doi: 10.1002/chem.201001204

BibTex

@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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