Abstract
AbstractIn this study, we report the synthesis of benzene‐glycol nucleic acids and studies of their biophysical and biological properties. Using (S)‐mandelic acid as the starting material, we prepared phosphoramidite units for the synthesis of benzene‐glycol nucleic acids. The benzene‐glycol moieties effectively replace the sugar groups ordinarily found in DNA and RNA monomers. Oligonucleotides (ONs) containing these nucleoside analogues formed thermally and thermodynamically stable duplexes with complementary DNA and RNA strands and proved to be more resistant (i.e. less susceptible) to 3′‐exonuclease than their “natural” counterparts. Furthermore, we demonstrated that a duplex composed of a modified ON and its complementary strand of RNA very effectively elicits RNase H activity.
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