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An Anti-Clostridium difficile Vaccine: Chemical Synthesis of the Pentasaccharide Repeating Unit of Polysaccharide PS-I

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Title: An Anti-Clostridium difficile Vaccine: Chemical Synthesis of the Pentasaccharide Repeating Unit of Polysaccharide PS-I
Author: Jiao, Yuening
Department: Department of Chemistry
Program: Chemistry
Advisor: Monteiro, Mario
Abstract: 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.
URI: http://hdl.handle.net/10214/3748
Date: 2012-06
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