5-Fluoro-2'-deoxycytidine as a Probe for the Study of B/Z-DNA Transition by ¹⁹F NMR Spectroscopy.

ABSTRACT: 5-Fluoro-2'-deoxycytidine was synthesized by treating 5-fluoro-2'-deoxyuridine with 2,4,6-trimethylphenol in the presence of 1-methylpyrrolidine and trifluoroacetic anhydride, followed by aminolysis. Among N-acetyl, pivaloyl, and benzoyl, N-acetyl was found to be suitable for the protection of the exocyclic amine of 5-fluoro-2'-deoxycytidine because of the stability of the N ⁴-protected nucleoside under acidic conditions and its ease of removal after solid-phase synthesis. This modified nucleoside was incorporated into d(CG)₆ sequences through the phosphoramidite chemistry-based solid-phase synthesis. Circular dichroism experiments suggest that replacement of 2'-deoxycytidine with 5-fluoro-2'-deoxycytidine does not lead to detectable conformationa

SUBMITTER: Solodinin A 

PROVIDER: S-EPMC6881825 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature