Sialosides specificity studies

High-Throughput Substrate Specificity Studies of Sialidases Using Chemoenzymatically Synthesized pNP-Tagged Sialosides... 

Chokhawala, H. A., Yu, H., and Chen, X., High-throughput substrate specificity studies of sialidases by using chemoenzymatically synthesized sialoside libraries. ChemBioChem... 

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... 

Lemieux GA, Yarema KJ, Jacobs CL, Bertozzi CR. Exploiting differences in sialoside expression for selective targeting of MRI contrast reagents. J. Am Chem. Soc. 1999 121 4278-4279. Gross HJ. Huorescent CMP-siaUc acids as a tool to study the specificity of the CMP-siaUc acid carrier and the glyco-conjugate sialylation in permeabilized cells. Eur. J. Biochem. 1992 203 269-275. 

Once chemoenzymatically produced, these unnatural sialosides have demonstrated utility in a variety of biological applications. A sialoside consisting of 9-0-acetylated sialyl Tn antigen (sTn) was produced by one-pot synthesis and conjugated to human serum albumin to be used to evaluate the role of acetylation in carbohydrate-protein interactions. Para-nitrophenol-tagged sialosides can be used in a colorimetric assay to evaluate sialidase specificity. Biotin-tagged sialosides have been immobilized on a streptavidin-coated surface to study protein-carbohydrate interactions with surface plasmon resonance techniques. Size-defined... 

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