Glycoconjugates, products of uridine derivatives phosphitylation and oxidation as glycosyltransferases potential inhibitors.

Acta Pol Pharm

Silesian University of Technology, Faculty of Chemistry, Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.

Published: February 2011

The title compounds, variously protected 5'-uridine derivatives connected with 1-thiosugar with thio-phosphoesters fragment (17-22) were synthesized in sequence of reactions: phosphitylation--reaction of 5'-hydroxyl group of selectively protected nucleoside with a phosphitylating agent (N,N-diisopropyl chlorophosphoamidite), connection an phosphoroamidites with 2-bromoethanol or 3-bromopropanol and secondary oxidation with sulfur presence and finally condensation reaction of obtained products with 1-thiosugar. Received glycoconjugates (17-22) had a structure which mimic to structure of natural glycosyltransferases substrates.

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