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Synthesis of E. faecium wall teichoic acid fragments
Daan van der Es1, Nadia A Groenia1, Diana Laverde2
1Leiden Institute of Chemistry, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands.
Bioorganic & Medicinal Chemistry
|March 20, 2016
Summary
Researchers synthesized Enterococcus faecium wall teichoic acid (WTA) fragments. This study identifies the sn-glycerol-3-phosphate stereochemistry in these crucial bacterial cell wall components.
Area of Science:
- Microbiology
- Organic Chemistry
- Immunology
Background:
- Enterococcus faecium possesses cell wall teichoic acids (WTA) crucial for its structure and function.
- Recent elucidation revealed WTA are glycerolphosphate (GroP)-based polymers with repeating units: -6-(GalNAc-α(1-3)-GalNAc-β(1-2)-GroP)-.
Purpose of the Study:
- To achieve the first synthesis of Enterococcus faecium wall teichoic acid (WTA) fragments.
- To determine the stereochemistry of the glycerolphosphate moiety in WTA.
Main Methods:
- Assembly of WTA fragments up to three repeating units in length.
- Stereoselective glycosylation reactions using galactosazide building blocks.
- NMR spectroscopy for structural comparison with isolated material.
Main Results:
- Successful synthesis of WTA fragments with varying glycerolphosphate stereochemistry.
- Identification of sn-glycerol-3-phosphate as the correct stereoisomer in the glycerol phosphate moiety.
- Generated fragments serve as tools for immunological studies.
Conclusions:
- The synthesis provides defined Enterococcus faecium WTA fragments.
- The sn-glycerol-3-phosphate stereochemistry of the glycerolphosphate moiety has been confirmed.
- These synthesized fragments are valuable for investigating WTA's role in host-pathogen interactions.
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