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Thomas Hartung

Publication Detail

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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 (Profiled Author: Thomas Hartung)

Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
Bioorganic & medicinal chemistry 2006;14(18):6239-54.

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 beta-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.

Scientific Context

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