Synthesis of the lipoteichoic acid of the streptococcus species DSM 8747

Qiao, Yan; Lindner, Buko; Zähringer, Ulrich; Truog, Peter; Schmidt, Richard R.

Synthesis of the lipoteichoic acid of the streptococcus species DSM 8747

Dateien

Schmidt_etal.pdfGröße: 1.13 MBDownloads: 359

Datum

2010

Autor:innen

Qiao, Yan

Lindner, Buko

Zähringer, Ulrich

Truog, Peter

Schmidt, Richard R.

Open Access-Veröffentlichung

Open Access Green

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Bioorganic & medicinal chemistry. 2010, 18(11), pp. 3696-3702. ISSN 0968-0896. eISSN 1464-3391. Available under: doi: 10.1016/j.bmc.2010.04.006

Zusammenfassung

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.

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

QIAO, Yan, Buko LINDNER, Ulrich ZÄHRINGER, Peter TRUOG, Richard R. SCHMIDT, 2010. Synthesis of the lipoteichoic acid of the streptococcus species DSM 8747. In: Bioorganic & medicinal chemistry. 2010, 18(11), pp. 3696-3702. ISSN 0968-0896. eISSN 1464-3391. Available under: doi: 10.1016/j.bmc.2010.04.006

BibTex

@article{Qiao2010Synth-375,
  year={2010},
  doi={10.1016/j.bmc.2010.04.006},
  title={Synthesis of the lipoteichoic acid of the streptococcus species DSM 8747},
  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 R.}
}

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