Synthesis of hexa- to tridecasaccharides related to Shigella dysenteriae type 1 for incorporation in experimental vaccines
| Autor: | Vince Pozsgay, Göran Ekborg, Srinivasa-Gopalan Sampathkumar |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
chemistry.chemical_classification
Glycosylation Shigella dysenteriae biology Stereochemistry Molecular Sequence Data Organic Chemistry O Antigens Oligosaccharides General Medicine Oligosaccharide HEXA biology.organism_classification Polysaccharide Biochemistry Analytical Chemistry chemistry.chemical_compound Carbohydrate Sequence Shigella Vaccines chemistry Polysaccharides Tetra Tetrasaccharide Trisaccharide |
| Zdroj: | Carbohydrate Research. 341:1408-1427 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2006.04.006 |
| Popis: | Hexa- to tridecasaccharides corresponding to the O-specific polysaccharide (O-SP) of the Gram-negative bacterium Shigella dysenteriae type 1 were synthesized in solution phase. The syntheses utilized tetra-, octa-, and dodecasaccharide intermediates that represent one to three contiguous tetrasaccharide repeating units of the O-SP [Synlett2003, 743]. These compounds were glycosylated with mono-, di-, and trisaccharide trichloroacetamidates, which were synthesized in this study. The excellent stereodirecting effect of 4,6-O-benzophenone ketals in glycosylation reactions of 2-azido-2-deoxy-glucopyranosyl donors was demonstrated. The free oligosaccharides were characterized by 1H and 13C NMR spectroscopy and by high-resolution mass spectrometry. The oligosaccharides described herein contain the 5-(methoxycarbonyl)pentyl aglycon for eventual attachment to immunogenic carriers using a recently published protocol [J. Org. Chem.2005, 70, 6987]. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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