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Convergent Synthesis of a Group B Streptococcus Type III Epitope Toward a Semisynthetic Carbohydrate-Based Vaccine.

Sam BahadoriMarie-Jeanne ArchambaultMathew SebastiaoSteve BourgaultDenis Giguère
Published in: The Journal of organic chemistry (2024)
In this work, we synthesized an hexasaccharide derived from the capsular polysaccharide of group B Streptococcus type III capsular polysaccharide. Our convergent 3 + 3 strategy avoided the use of benzyl protecting groups allowing the installation of an azide anchoring group and providing a high yield for the final deprotection steps. Moreover, the minimal hexasaccharidic epitope was conjugated to CRM 197 and BSA via copper-catalyzed azide-alkyne cycloaddition for the preparation of a semisynthetic carbohydrate-based vaccine.
Keyphrases
  • type iii
  • biofilm formation
  • candida albicans
  • monoclonal antibody
  • photodynamic therapy
  • staphylococcus aureus
  • pseudomonas aeruginosa
  • escherichia coli
  • water soluble
  • mass spectrometry
  • cystic fibrosis
  • high resolution