Synthesis of Benzene‐Glycol Nucleic Acids and Their Biophysical and Biological Properties

Abstract

Abstract:In this study, we report the synthesis of benzeneglycol 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

Synthesis of the Phosphoramidite Units for Benzene‐Glycol Nucleic Acid

“…The oligonucleotides can form stable duplex with complementary RNA, but DNA‐GNA chimeras show lower thermal stability than native DNA oligomer (Schlegel et al., ). Based on these results, the authors have recently designed the benzene‐glycol nucleic acid (BGNA) and reported the synthesis and properties of BGNA‐DNA chimeras (Niwa, Ueda, & Ueno, , in press). BGNA‐DNA‐BGNA gapmers form thermally and thermodynamically stable duplexes with complementary RNA strands and have base‐discriminating abilities.…”