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A series of glycoconjugates with defined connectivity were synthesized to investigate the impact of coupling Salmonella typhimurium O-antigen to different amino acids of CRM197 protein carrier. In particular, two novel methods for site-selective glycan conjugation were developed to obtain conjugates with single attachment site on the protein, based on chemical modification of a disulfide bond and pH-controlled transglutaminase-catalyzed modification of lysine, respectively. Importantly, conjugation at the C186-201 bond resulted in significantly higher anti O-antigen bactericidal antibody titers than coupling to K37/39, and in comparable titers to conjugates bearing a larger number of saccharides. This study demonstrates that the conjugation site plays a role in determining the immunogenicity in mice and one single attachment point may be sufficient to induce high levels of bactericidal antibodies.

Original publication

DOI

10.1002/anie.201506112

Type

Journal article

Journal

Angew Chem Int Ed Engl

Publication Date

02/11/2015

Volume

54

Pages

13198 - 13203

Keywords

carbohydrates, glycoproteins, protein modification, solmonella, vaccines, Animals, Female, Glycoconjugates, Mice, Mice, Inbred C57BL, Models, Molecular, Molecular Conformation, O Antigens, Salmonella Vaccines, Salmonella typhimurium