Partial acylation of cytidine and its 2'-C-methyl analogue as a tool to functionalize the ribonucleosidic 2’,3’-cis-diol system

Abstract

Dedicated to Professor Harri Lönnberg on the occasion of his 60 th anniversary AbstractPrecisely controlled conditions of acylation and 2',3'-O-isomerization allowed to synthesize tripivaloyl derivatives of cytidine with free 2'-or 3'-hydroxyl group in a simple manner. Acylation of 2'-C-β-methylcytidine proceeded in a different way and resulted in the formation of tripivaloyl 2'-hydroxy nucleoside, or dipivaloyl 2',3'-dihydroxy compound. All these products may be applied as key intermediates in the regioselective modification of 2',3'-cis-diol system.

Application of Molecular Dynamics Simulations to the Design of Nucleotide Inhibitors Binding to Norovirus Polymerase

“…Compound aa101 has been previously investigated for possible inhibition of the hepatitis C virus and of yellow fever virus in replicon assays and was found to be ineffective and also to have low toxicity. 36 While neither of the corresponding nucleosides was active in our NoV RdRp replicon assay, both were found to be chain terminators of NoV RdRp in the triphosphate form (Figure 6). A lack of either phosphorylation within the cells or cellular uptake is most likely responsible for the inactivity of the compounds in the replicon assay.…”

A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

“…Support from the Ministry of Education and Research of Estonia (grant IUT [19][20][21][22][23][24][25][26][27][28][29][30][31][32] and the EU Regional Development Fund Grant (3.2.0101.08-0017) are acknowledged. Notes and references…”

“…13 C NMR (100.6 MHz, CDCl 3 ) δ 178 23,. 178.08, 156.10 (broad), 140.21 (broad), 86.78, 81.74, 74.34, 64.05, 42.15, 39.02, 38.86, 38.79, 27.45, 27.33, 27.11 (signals from two carbons of the cytosine ring and quaternary carbon of the pivaloylamide carbonyl group were not detected due to strong line broadening and low intensity).…”