title: Glycoconjugates, products of uridine derivatives phosphitylation and oxidation as glycosyltransferases potential inhibitors.
abstract: 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.
authors.affiliation: Silesian University of Technology, Faculty of Chemistry, Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Krzywoustego 4, 44-100 Gliwice, Poland.
authors.forename: Marta
authors.initials: M
authors.lastname: Grec
authors.forename: Piotr
authors.initials: P
authors.lastname: Swierk
authors.forename: Gabriela
authors.initials: G
authors.lastname: Pastuch
authors.forename: Wiesław
authors.initials: W
authors.lastname: Szeja
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D016695:Glycosyltransferases / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D006001:Glycoconjugates; D016695:Glycosyltransferases; D014529:Uridine