Oligosaccharides play a fundamental role in mammalian cell in many important biological processes for example immune recognition, cell-cell communication and initiation of microbial pathogenesis and are commonly found as glycoconjugates (glycoproteins or glycolipids) [1]. Glycosyltransferases belong to the family of enzymes that create glycosidic bonds in nature. With regard for importance glycoconjugates in function of mammalian cell, control of activity of glycosyltransferases is interesting and evolving course of action.

Previously we proposed protected 5’-uridine derivatives connected with (5-amino-2-pyridyl) 1-thio-β-D-glycosides with a succinic linker as analogues of GTs natural substrate with potential inhibition activity [2]. Some of them were tested for ability to inhibition the propagation of classical swine fever virus (CSFV). Reduction of the number CSFV-infected cells was observed without significant toxicity for mammalian cells. Encouraged these positive results we made new scale of compounds, in which variously protected 5’-uridine derivatives connected with 1-thiosugars with thiophosphoesters fragment. 

First stage was phosphitylation – reaction 5’-hydroxyl group of selective protected nucleoside with a phosphitylating agent (N,N-diisopropyl chlorophosphoamidite). We coupled an anomeric phosphoramidites with 2-bromoethanol or 3-bromopropanol and then we oxidized these intermediates with sulphur presence. In next step we used these products to reaction of condensation with 1-thiosugars and received glycoconjugates with potential inhibition activity, which structure was mimic to structure of natural glycosyltrnasferases substrates.

Acknowledgement

Research studies part-financed by the European Union within the European Regional Development Fund (POIG. 01.01.02-14-102/09).

[1] Weijers C.A.G.M.; Franssen M.C.R.; Visser G.M.; Biotech. Adv. 2008, 26, 436-456

[2] Pastuch-Gawołek G.; Bieg T.; Szeja W.; Flasz J.; Bioorg. Chem. 2009, 37, 77-83

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