β-Cyanuryl Ribose, β-Barbituryl Ribose, and 6-Azauridine as Uridine Mimetics.

ABSTRACT: Uridine (U) mimetics are sought after as tools for biochemical and pharmacological studies. Previously, we have identified recognition patterns of U by proteins. Here, we targeted the characterization of uridine mimetics-cyanuryl-ribose (CR), barbituryl-ribose (BR), and 6-azauridine (AU)-with a view to identify analogs with potentially more binding interactions than U with target biomolecules. We found that CR, BR, and AU retain selective U's natural H-bonds with adenosine vs guanosine. CR/AU and BR were 100- and 10,000-fold more acidic, respectively, than U. Under physiological pH, 54, 51, and 77% of CR, AU, and BR molecules, respectively, are ionized vs 13% for U. The electron-rich nature of CR and BR vs U was reflected by their ¹³C NMR chemical shifts and ε values. CR/AU and

SUBMITTER: Salameh H 

PROVIDER: S-EPMC7726947 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature