1 research outputs found
Straightforward Synthesis of Purine 4′-Alkoxy-2′-deoxynucleosides: First Report of Mixed Purine–Pyrimidine 4′-Alkoxyoligodeoxynucleotides as New RNA Mimics
Purine and pyrimidine 4′-alkoxy-2′-deoxynucleosides
were efficiently prepared from nucleoside 4′-5′-enol
acetates in three steps by <i>N</i>-iodosuccinimide promoted
alkoxylation, hydrolysis, and reduction followed by conversion to
phosphoramidite monomers for the solid-phase synthesis of the oligonucleotides.
Fully modified 4′-alkoxyoligodeoxynucleotides, which are characterized
by a prevalent <i>N</i>-type (RNA-like) conformation, exhibited
superior chemical and nuclease resistance as well as excellent hybridization
properties with a strong tendency for RNA-selective hybridization,
suggesting a potential application of 4′-alkoxy-oligodeoxynucleotides
in antisense technologies