Polysaccharide conjugated vaccines have benefited billions of people by inducing an adaptive immune response to prevent virulent bacterial infections. Reductive amination is one of the most widely used conjugation chemistries for manufacturing such vaccines. However, due to the complex nature of polysaccharide conjugated proteins, detailed structural characterization of the conjugates has been elusive. Recent studies, using model compounds, have brought new insights into the potential structure of these vaccines when using reductive amination chemistry.  Our data suggest that an oxazepane type ring is formed in the conjugation reaction between the polysaccharide and the protein.  Two different carbohydrate systems were examined, each pointing to the same mechanism.  During these experiments, it was also found that of the 39 lysines in the CRM<sub>197</sub>-carrier protein, certain lysines are more reactive than others under aqueous conditions. Our study can benefit vaccine design and provide more detailed structural understanding of carbohydrate protein conjugate vaccines.<br/>

Building heightened characterization for conjugate vaccines through carbohydrate-peptide/CRM model studies

ACS Fall 2020 Virtual Meeting

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