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

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

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STADELMAIER, Andreas, Ignacio FIGUEROA-PEREZ, Susanne DEININGER, Sonja von AULOCK, Thomas HARTUNG, Richard R. SCHMIDT, 2006. A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues. In: Bioorganic & Medicinal Chemistry. 14(18), pp. 6239-6254. ISSN 0968-0896. Available under: doi: 10.1016/j.bmc.2006.05.055

@article{Stadelmaier2006Staph-8786, title={A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues}, year={2006}, doi={10.1016/j.bmc.2006.05.055}, number={18}, volume={14}, issn={0968-0896}, journal={Bioorganic & Medicinal Chemistry}, pages={6239--6254}, author={Stadelmaier, Andreas and Figueroa-Perez, Ignacio and Deininger, Susanne and Aulock, Sonja von and Hartung, Thomas and Schmidt, Richard R.} }

Figueroa-Perez, Ignacio 2011-03-24T17:46:27Z Schmidt, Richard R. eng A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues Schmidt, Richard R. 2011-03-24T17:46:27Z 2006 Stadelmaier, Andreas Figueroa-Perez, Ignacio Hartung, Thomas Deininger, Susanne Stadelmaier, Andreas Hartung, Thomas Aulock, Sonja von application/pdf terms-of-use Deininger, Susanne Aulock, Sonja von First publ. in: Bioorganic & Medicinal Chemistry 14 (2006), 18, pp. 6239-6254 Based on 1,2 O isopropylidene O 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.

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