Synthesis of E. faecium wall teichoic acid fragments. Issue 17 (1st September 2016)

• Record Type: Journal Article
• Authors: van der Es, Daan; Groenia, Nadia A.; Laverde, Diana; Overkleeft, Herman S.; Huebner, Johannes; van der Marel, Gijsbert A.; Codée, Jeroen D.C.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 24:Issue 17(2016)
• Page Start: 3893
• Page End: 3907
• Publication Date: 2016-09-01
• Subjects: E. faecium -- Wall teichoic acid -- Carbohydrate -- Glycosylation -- Phosphoramidite; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2016.03.019
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: The first synthesis of different Enterococcus faecium wall teichoic acid (WTA) fragments is presented. The structure of these major cell wall components was elucidated recently and it was shown that these glycerolphosphate (GroP) based polymers are built up from -6-(GalNAc-α(1–3)-GalNAc-β(1–2)-GroP)- repeating units. We assembled WTA fragments up to three repeating units in length, in two series that differ in the stereochemistry of the glycerolphosphate moiety. The key GalNAc-GalNAc-GroP synthons, required for the synthesis, were generated from galactosazide building blocks that were employed in highly stereoselective glycosylation reactions to furnish both the α- and β-configured linkages. By comparing the NMR spectra of the synthesized fragments with the isolated material it appears that the hereto undefined stereochemistry of the glycerol phosphate moiety is sn -glycerol-3-phosphate. The generated fragments will be valuable tools to study their immunological activity at the molecular level.