Enzymatic synthesis of 3'-fluorinated sialosides

CARB 76

Harshal A. Chokhawala, Hongzhi Cao, hzcao@ucdavis.edu, Hai Yu, hyu@ucdavis.edu, and Xi Chen, chen@chem.ucdavis.edu. Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, CA 95616
Sialic acids play important roles in cell-cell interaction, recognition, infection and tumor metastasis. Due to terminal position of these sialic acids they serve as important recognition elements in these processes. Studying the sialic acid-protein interaction (sialidases, haemagglutinins, siglecs and selectins) at the molecular level has become imperative to understand these biological processes mediated by such interactions. In order to understand sialic acid – sialidase interactions we were interested in making sialosides that are resistant to hydrolysis by sialidases since such compounds would serve well as molecular probes for studying the active site conformation of sialidases in complex with such non-hydrolysable substrate analogs. Towards this end we have enzymatically synthesized sialic acid oligosaccharides (sialosides) having fluorine at the C-3 of sialic acid, which would retard the rate of hydrolysis of such sialosides by sialidases. In addition such compounds could also serve as an important class of inhibitors that inhibit sialidases and haemagglutinins.
 

General Posters
6:00 PM-8:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Carbohydrate Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007