Oxazolidinone protected sialosyl donor and acceptor for the stereoselective synthesis of alpha-sialosides

CARB 60

Cristina De Meo, cdemeo@siue.edu, Michael Farris, mfarris@siue.edu, and Nathan Ginder, nginder@siue.edu. Department of Chemistry, Southern Illinois University Edwardsville, BOX 1652, Edwardsville, IL 62026
Sialic acids are a family of about 50 naturally occurring 2-keto-3-deoxy-nononic acids involved in a wide range of biological processes. Sialic acid-containing glycoconjugates are implicated in a large number of biological phenomena such as cell-cell adhesion, cell growth regulation, immune response, and oncogenesis. As a part of a program to develop new strategies for the synthesis of alpha-sialosides, we propose the synthesis of an oxazolidinone protected thioglycoside sialosyl donor and the study of its influence on the yield and stereoselectivity in glycosylation reactions. For the synthesis of alpha-(2-8)dimers, a sialosyl acceptor bearing an oxazolidinone fused-ring was also synthesized and its reactivity compared to common acceptors.

 

General Posters
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Carbohydrate Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006