Synthesis of Staphylococcus aureus type 5 capsular polysaccharide repeating unit using novel L-FucNAc and D-FucNAc synthons and immunochemical evaluation
| Autor: | Luigi Lay, Elisa Danieli, Francesco Berti, Emilia Cappelletti, Daniela Proietti, Paolo Costantino, Marta Tontini, Roberto Adamo, Giulia Brogioni, Maria Rosaria Romano |
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| Rok vydání: | 2012 |
| Předmět: |
Antigenicity
Glycoconjugate Clinical Biochemistry Pharmaceutical Science Dot blot Enzyme-Linked Immunosorbent Assay Polysaccharide medicine.disease_cause Biochemistry Antigen-Antibody Reactions Mice Drug Discovery medicine Animals Trisaccharide Molecular Biology Bacterial Capsules Fucose chemistry.chemical_classification Immunochemistry Organic Chemistry Polysaccharides Bacterial Blot Uronic Acids chemistry Staphylococcus aureus Molecular Medicine Female Conjugate |
| Zdroj: | Bioorganicmedicinal chemistry. 20(21) |
| ISSN: | 1464-3391 |
| Popis: | Staphylococcus aureus is a major cause of nosocomial infections. Glycoconjugates of type 5 and 8 capsular polysaccharides have been investigated for vaccine application. The proposed structure of type 5 polysaccharide is: →4-β-D-ManNAcA-(1→4)-α-L-FucNAc(3OAc)-(1→3)-β-D-FucNAc-(1→. The stereocontrolled insertion of these three glycosydic bonds is a real synthetic challenge. In the present paper we report the preparation of two novel versatile L- and D-fucosamine synthons from commercially available starting materials. In addition we applied the two building blocks to the synthesis of type 5 trisaccharide repeating unit. The immunochemical properties of the synthesized trisaccharide were assessed by competitive ELISA and by immunodot blot analysis using sera of mice immunized with type 5 polysaccharide conjugated to CRM(197). The results suggest that although the type 5 S. aureus trisaccharide is recognized by specific anti polysaccharide antibodies in dot blot, structures longer than the trisaccharide may be needed in order to significantly compete with the native type 5 polymer in the binding with sera from mice immunized with S. aureus type 5 polysaccharide-CRM(197) conjugate. |
| Databáze: | OpenAIRE |
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