Type of Publication: | Journal article |
URI (citable link): | http://nbn-resolving.de/urn:nbn:de:bsz:352-opus-130729 |
Author: | Qiao, Yan; Lindner, Buko; Zähringer, Ulrich; Truog, Peter; Schmidt, Richard |
Year of publication: | 2010 |
Published in: | Bioorganic & medicinal chemistry ; 18 (2010), 11. - pp. 3696-3702. - ISSN 0968-0896. - eISSN 1464-3391 |
Pubmed ID: | 20510791 |
DOI (citable link): | https://dx.doi.org/10.1016/j.bmc.2010.04.006 |
Summary: |
The lipoteichoic acid (LTA) of the Streptococcus species DSM 8747 consists of a Beta-D-galactofuranosyl diacylglycerol moiety (with different acyl groups) that is linked via 6-0 to a poly(glycerophosphate) backbone; about 30% of the glycerophosphate moieties carry at 2-0 hydrolytically labile o-alanyl residues. As typical LTA for this array of compounds LTA la was synthesized. To this end, from o-galactose the required galactofuranosyl building block 5 was obtained. The anomeric stereocontrol in the glycosylation step with 1,2-0-cyclohexylidene-sn-glycerol (4) was based on anchimeric assistance, thus finally leading to the unprotected core glycolipid 16. Regioselective protection and de protection procedures permitted the defined attachment of the pentameric glycerophosphate 3 to the 6-hydroxy group of the galactose residue. Introduction of four D-alanyl residues led after global deprotection and purification to target molecule la possessing on average about two D-alanyl residues at 2-0 of the pentameric glycerophosphate backbone, thus being in close accordance with the structure of the natural material.
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Subject (DDC): | 540 Chemistry |
Controlled Keywords (GND): | Lipoteichoic acid (LTA), synthesis, glycosidation, glycophospholipids, gram-positive bacteria |
Link to License: | In Copyright |
QIAO, Yan, Buko LINDNER, Ulrich ZÄHRINGER, Peter TRUOG, Richard SCHMIDT, 2010. Synthesis of the lipoteichoic acid of the streptococcus species DSM 8747. In: Bioorganic & medicinal chemistry. 18(11), pp. 3696-3702. ISSN 0968-0896. eISSN 1464-3391. Available under: doi: 10.1016/j.bmc.2010.04.006
@article{Qiao2010Synth-375, title={Synthesis of the lipoteichoic acid of the streptococcus species DSM 8747}, year={2010}, doi={10.1016/j.bmc.2010.04.006}, number={11}, volume={18}, issn={0968-0896}, journal={Bioorganic & medicinal chemistry}, pages={3696--3702}, author={Qiao, Yan and Lindner, Buko and Zähringer, Ulrich and Truog, Peter and Schmidt, Richard} }
Schmidt_etal.pdf | 463 |