Sialic acid immunogenicity

The latter approach has been followed in our laboratory. For instance, in studies related to the synthesis of potent multivalent sialoside inhibitors of influenza virus hemagglutinin [34], it became of interest to evaluate the immunogenicity of neoglycoproteins containing sialosides as sole immunodominant hapten. To this end, acetochloroneuraminic acid (1) was transformed into allyl glycoside 2 (Scheme 1) which upon reductive ozonolysis afforded aldehyde 3 in excellent overall yields [35], Reductive amination of 3 to bovine serum albumin (BSA) and tetanus toxoid provided immunogenic vaccines from which specific rabbit IgG anti-sialic acid antibodies were obtained [36]. In order... 

Thio-linked sialic acid has been used to reduce immunogen degradation (138). Gangliosides are shed by tumor cells and antibodies to such GSLs are considered of potential therapeutic benefit, and these have been raised via ganglioside-protein conjugate vaccines (139, 140). 

Tangvoranuntakul P, Gagneux P, Diaz S, Bardor M, Varki N, Varki A, Muchmore E (2003) Human uptake and incorporation of an immunogenic nonhuman dietary sialic acid. Proc Natl Acad Sci USA 100 12045-12050... 

Martin, M. J., Muotri, A., Gage, E, and Varki, A. 2005. Human embryonic stem cells express an immunogenic nonhuman sialic acid. Nat Med, 11, 228-32. 

---