Вид документа : Статья из журнала Шифр издания : Автор(ы) : Konstantinova I. D., Selezneva O. M., Kotovskaya S. K., Baskakova Z. M., Charushin V. N., Baranovsky A. V., Fateev I. V., Balashova T. A., Balzarini J., Mikhailopulo I. A. Заглавие : Chemo-Enzymatic Synthesis and Biological Evaluation of 5,6-Disubstituted Benzimidazole Ribo- and 2′-Deoxyribonucleosides Место публикации : Synthesis. - 2013. - Vol.45, № 2. - С. 272-280 Ключевые слова (''Своб.индексиров.''): 5,6-disubstituted benzimidazoles--nucleosides--purine nucleoside phosphorylase Аннотация: A number of new 5,6-disubstituted benzimidazoles have been prepared and their substrate properties for recombinant E. coli purine nucleoside phosphorylase (PNP; the product of the deoD gene) in the transglycosylation reaction were investigated. The heterocyclic- bases showed good substrate activity for PNP and the ribo- and 2′-deoxyribonucleosides were synthesized. The predominant (OMe and OEt) or exclusive (Oi-Pr, morpholino, and N-methylpiperazino) formation of the 5-substituted 6-fluoro-1-(β-D-ribofuranosyl)benzimidazoles was observed. The formation of the regioisomeric 6- methoxy-, 6-ethoxy-, or 6-isopropoxy-substituted 1-(2-deoxy-β-D-ribofuranosyl)-5-fluorobenzimidazoles was observed in the trans-2-deoxyribosylation reaction of the corresponding bases. The predominant or exclusive formation of the regioisomeric N1-nucleosides with bulky 5-substituents of 6-fluorobenzimidazole points to a large hydrophobic pocket in the E. coli PNP active site that can accommodate these groups. The biological activity of the synthesized nucleosides was studied and revealed no inhibitory activity against a broad variety of DNA and RNA viruses. The compounds also lacked significant cy Доп.точки доступа: Konstantinova, I. D.; Selezneva, O. M.; Kotovskaya, S. K.; Baskakova, Z. M.; Charushin, V. N.; Baranovsky, A. V.; Fateev, I. V.; Balashova, T. A.; Balzarini J.; Mikhailopulo, I. A.