A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues

A. Stadelmaier, I. Figueroa-Perez, S. Deininger, S. von Aulock, T. Hartung, R. R. Schmidt

Research output: Contribution to journalArticle

Abstract

Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl β-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which d-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA.

Original languageEnglish (US)
Pages (from-to)6239-6254
Number of pages16
JournalBioorganic and Medicinal Chemistry
Volume14
Issue number18
DOIs
StatePublished - Sep 15 2006
Externally publishedYes

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Keywords

  • Bacteria
  • Bisamphiphilic
  • Cytokine release
  • Gram-positive
  • Lipoteichoic acid
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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