title: 5-Nitro-2-pyridyl-1-thioglucosides: application in synthesis of analogues of glycosyltransferases natural substrates.
abstract: 5-Nitro-2-pyridyl-1-thioglucosides were used in synthesis of complex uridine derivatives (13-16) in two different sequences of reactions. In one route, the first step was glycosylation of selectively protected 5-nitro-2-pyridyl-1-thioglucoside 1 with two different glycosyl donors (5 or 6), next, the nitro group in aglycone of obtained disaccharides 7 or 8 was reduced and then obtained products 9 or 10 were condensed with uridine derivatives 3 or 4 using DMT-MM as condensing agent under microwave irradiation. In the second route, condensation and glycosylation reactions were applied in reverse order. As it turned up, a sequence of reactions affected the yield of final glycoconjugates 13-16 and depended on the type of uridine derivatives used.
authors.affiliation: Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Faculty of Chemistry, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland. gabriela.pastuch@polsl.pl
authors.forename: Gabriela
authors.initials: G
authors.lastname: Pastuch
authors.forename: Roman
authors.initials: R
authors.lastname: Komor
authors.forename: Marta
authors.initials: M
authors.lastname: Grec
authors.forename: Wiesław
authors.initials: W
authors.lastname: Szeja
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D006031:Glycosylation; D016695:Glycosyltransferases / Q000037:antagonists & inhibitors / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D013863:Thioglucosides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D013891:Thiouridine / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D013863:Thioglucosides; D013891:Thiouridine; D016695:Glycosyltransferases