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Lecture 5

CHEM564 Lecture 5: Case study.5

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University of Alberta
Christopher Cairo

BioconjugateChemistry Cairo 6.1.5 Conjugate vaccines: Linking carbohydrates to proteins The use of bioconjugates for the development of vaccines is a common strategy. This is most critical for antigens that may be hard to generate synthetically. The best example is likely the polysaccharides produced by bacteria. These polysaccharides are often unique to certain species and distinct from human saccharides, providing a selective antigen for use in a vaccine. Reviews of glyconjugate vaccines discuss specific issues related to the selection of antigens and 36-38 generation of a successful vaccine conjugate. The first glycoconjugate vaccine was reported by Avery & Goedel in 1931, in which they conjugated the polysaccharide of pneumococcus to proteins. 39, 4Their strategy exploited non- specific reaction of hydroxyl groups on the polysaccharide, converting them to diazo groups using a benzyl linker. The diazo group could then react with Tyr residues of the protein to generate a stable linkage. The use of diazo chemistry to specif ically modify Tyr or Trp residues 41 has since been developed as a more specific protein-modification strategy. The development of the conjugate vaccine for meningococcal infections was reported in 1981 by researchers at the National Research Council of Canada. 42, 4The chemistry used involved isolation of the capsular polysaccharide (CPS) from the bacteria, followed by its conjugation using either reductive amination or sodium periodate chemistry. 43 The meningococcal CPS 235 BioconjugateChemistry Cairo contains a poly-sialic acid, which allows selective oxidation of the terminal sialic acid. The CPS polysaccharide is then conjugated to an immunogenic protein. The protein used here was the tetanus toxoid protein (TT). HO OH COO - COO-
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