Synthesis of Staphylococcus aureus Type 5 trisaccharide repeating unit: solving the problem of lactamization
| Autor: | Gagarinov, Ivan A, Fang, Tao, Liu, Lin, Srivastava, Apoorva D, Boons, Geert-Jan, Sub Chemical pharmacology, Sub Algemeen Scheikunde, Medicinal Chemistry and Chemical Biology |
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| Přispěvatelé: | Sub Chemical pharmacology, Sub Algemeen Scheikunde, Medicinal Chemistry and Chemical Biology |
| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
chemistry.chemical_classification
Staphylococcus aureus Glycosylation Molecular Structure Organic Chemistry Polysaccharides Bacterial Late stage Bacterial medicine.disease_cause Biochemistry Chemical synthesis Combinatorial chemistry Article chemistry Polysaccharides medicine Moiety Organic chemistry Trisaccharide Physical and Theoretical Chemistry Trisaccharides |
| Zdroj: | Organic Letters, 17(4), 928. American Chemical Society : Division of Carbohydrate Chemistry |
| ISSN: | 1523-7060 |
| Popis: | The chemical synthesis of an orthogonally protected trisaccharide derived from the polysaccharide of Staphylococcus aureus Type 5, which is an attractive candidate for the development of immunotherapies, is described. The challenging α-fucosylation and β-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a β-D-ManpNAcA moiety during deprotection was avoided by a late stage oxidation approach. Versatility of the trisaccharide was demonstrated by its transformation into a spacer-containing repeating unit suitable for immunological investigations. |
| Databáze: | OpenAIRE |
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