Trifluoromethyl analogs of fucose and uses thereof
AssigneeThe Biomembrane Institute
InventorsTatsushi Toyokuni, Sen-itiroh Hakomori
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Abstract
The present invention discloses trifluorofucoses and methods of making the same. Also disclosed are trifluorofucose analogs of fucose-containing oligosaccharides, and conjugates of trifluorofucose. Compositions are prepared which combine the trifluorofucose-containing oligosaccharides or trifluorofucose conjugates of the present invention with a pharmaceutically acceptable carrier or diluent. Tumor cell metastasis, autoimmune responses or inhibition of an inflammatory process may be inhibited by such compositions.
Claims6
A compound having the formula:
- ##STR5## wherein R and R' are H or OH, but are not both H or both OH.
A method for the synthesis of 6,6,6-trifluorofucose comprising the steps of:
- (a) reacting a perbenzylated acyclic aldehyde derivative of lyxose with trifluoromethyltrimethylsilane to form trifluoromethylated siloxy adducts of lyxose;
- (b) hydrolyzing said siloxy adducts with about 1M hydrochloric acid to form desilylated adducts;
- (c) reducing said desilylated adducts by catalytic hydrogenation with palladium hydroxide to form deperbenzylated alcohols;
- (d) subjecting said alcohols to pertrimethylsilylation to form trimethylsiloxy adducts;
- (e) oxidizing said trimethylsiloxy adducts with (CrO.sub.3 -pyridine complex) to form trimethylsiloxy aldehydes;
- (f) desilylating said trimethylsiloxy aldehydes to form a mixture of 6,6,6-trifluorofucose and 6-deoxy-6,6,6-trifluoroaltrose;
- and
- (g) recovering said 6,6,6-trifluorofucose.
A trifluorofucose analog of a fucose-containing oligosaccharide comprising an oligosaccharide selected from the group consisting of Le.sup.x, sialyl Le.sup.x, disialyl Le.sup.x, dimeric Le.sup.x, sialyl-dimeric Le.sup.x, trifucosyl Le.sup.x, and Le.sup.y, wherein at least one of the fucoses has been substituted with 6,6,6-trifluorofucose.
A trifluorofucose analog of a fucose-containing oligosaccharide, wherein at least one of the fucoses has been substituted with 6,6,6-trifluorofucose.
Dependencies are inferred from the claim text.