Clostridium difficile is a Gram-positive bacterium that is the most common cause of hospital-associated and antimicrobial-associated diarrhea in humans. Monteiro and co-workers have discovered that C. difficile expresses three cell-surface polysaccharides, named PS-I, PS-II and PS-III. Interestingly, PS-I was determined to be present in a ribotype 027 strain, the ribotype responsible for recent deadly outbreaks worldwide. In this work, the total chemical synthesis of the PS-I pentasaccharide with a linker molecule by a linear synthesis strategy from four monosaccharide building blocks is described:
α-L-Rhap-(1→3)-β-D-Glcp-(1→4)-α-D-Glcp-(1→2)-α-D-Glcp-(1→O(CH2)5NH2
3
↑
1
α-L-Rhap
The synthesized PS-I pentasaccharide will be conjugated to a protein carrier for evaluation as an anti-C. difficile glycoconjugate vaccine.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:OGU.10214/3748 |
| Date | 22 June 2012 |
| Creators | Jiao, Yuening |
| Contributors | Monteiro, Mario |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Thesis |
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