Journal
CARBOHYDRATE RESEARCH
Volume 344, Issue 5, Pages 570-575Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2008.12.021
Keywords
Polysaccharide intercellular adhesin; Glycoconjugates; Neoglycoproteins
Funding
- Natural Science & Engineering Research Council (NSERC) of Canada
- Canadian Institutes of Heath Research (CIHR)
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A wide variety of medically important biofilm forming bacteria produce similar polysaccharide intracellular adhesins (PIAs). The PIA structures consist of partially de-N-acetylated beta-(1 -> 6)-N-acetylglucosamine polymers. These exopolysaccharides are key components of the bacterial biofilm matrix. Here, we describe the efficient synthesis of PIA oligosaccharides using an acid reversion reaction of N-acetylglucosamine in HF pyridine. The PIA oligosaccharides produced by this reaction can be purified to homogeneity by size exclusion chromatography. Chemistry was developed to conjugate the PIA oligosaccharides to bovine serum albumin using a new heterobifunctional linker containing a thiol and an N-methylhydroxylamine functional group. These glycoconjugates may serve as useful precursors for the development of defined conjugate vaccines against PIA producing bacterial strains. (C) 2009 Elsevier Ltd. All rights reserved.
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