Synthesis of nonnatural UDP-sugars for the enzymatic preparation of well defined heparin-like oligosaccharides

CARB 70

Michel Weïwer, weiwen@rpi.edu1, Fei Huang1, and Robert J. Linhardt, Linhar@rpi.edu2. (1) Department of Chemistry and Biological Chemistry, Rensselaer Polytechnic Institute, 110 8th Street, Troy, NY 12180, (2) Departments of Chemistry and Chemical Biology, Rensselaer Polytechnic Institute, Biotech Center 4005,110 8th Street, troy, NY 12180
A better understanding of heparin interaction with a large number of proteins relies on the availability of well-defined, heparin-like oligosaccharides. Particularly, the sulfation pattern is of great importance. To achieve this goal, the enzymatic preparation of heparin-like oligosaccharides represents an interesting alternative to the complex purification processes. In this context, a number of UDP-hexosamines and UDP-uronic acids derivatives are needed as building blocks. In initial studies, we have been interested in the synthesis of non-natural UDP-glucosamines, where the acetamido group and/or the C-6 position has been modified for further sulfonation. This would allow, for example, the differentiation of the amino group of one glucosamine unit in an oligosaccharide. In subsequent studies, we have begun to synthesize UDP-GlcA derivatives.
 

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

Division of Carbohydrate Chemistry

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