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

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

doi:10.1016/j.tet.2011.11.088

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

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

Department of Chemistry

10 Citations (Scopus)

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).

Original language	English
Journal	Tetrahedron
Volume	68
Issue number	4
Pages (from-to)	1052-1061
Number of pages	10
ISSN	0040-4020
DOIs	https://doi.org/10.1016/j.tet.2011.11.088
Publication status	Published - 28 Jan 2012

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title = "Synthesis of the repeating unit of the lipoteichoic acid of Streptococcus pneumoniae",

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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T1 - Synthesis of the repeating unit of the lipoteichoic acid of Streptococcus pneumoniae

AU - Pedersen, Christian Marcus

AU - Figueroa-Perez, Ignacio

AU - Ulmer, Artur J.

AU - Zähringer, Ulrich

AU - Schmidt, Richard R.

PY - 2012/1/28

Y1 - 2012/1/28

N2 - 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).

AB - 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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DO - 10.1016/j.tet.2011.11.088

M3 - Journal article

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VL - 68

SP - 1052

EP - 1061

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

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

Abstract

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