Site of Azido Substitution in the Sugar Moiety of Azidopyrimidine Nucleosides Influences the Reactivity of Aminyl Radicals Formed by Dissociative Electron Attachment.

ABSTRACT: In this work, electron-induced site-specific formation of neutral π-type aminyl radicals (RNH·) and their reactions with pyrimidine nucleoside analogs azidolabeled at various positions in the sugar moiety, e.g., at 2'-, 3'-, 4'-, and 5'- sites along with a model compound 3-azido-1-propanol (3AZPrOH), were investigated. Electron paramagnetic resonance (EPR) studies confirmed the site and mechanism of RNH· formation via dissociative electron attachment-mediated loss of N₂ and subsequent facile protonation from the solvent employing the ¹⁵N-labeled azido group, deuterations at specific sites in the sugar and base, and changing the solvent from H₂O to D₂O. Reactions of RNH· were investigated employing EPR by warming these samples from 77 K to ca. 170

SUBMITTER: Mudgal M 

PROVIDER: S-EPMC7746630 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature