Synthesis and hybridization properties of an oligonucleotide analog containing a glucose-derived conformation-restricted ribose moiety and 2', 5' formacetal linkages

Article abstract of DOI:10.1016/0040-4039(95)02396-8

A pyrimidine trinucleoside containing a conformationally restricted ribose moiety and two 2', 5' formacetal internucleoside linkages was synthesized. The bicyclic ribose moiety was identified by molecular modeling as a candidate to preorder a nucleoside to resemble the bound duplex conformation. The thymine nucleoside analog was simply synthesized from glucose. The trimer was incorporated at the 3' end of a larger unmodified ON. The hybridization affinity of this chimeric ON analog to a complementary RNA was found to be somewhat inferior relative to a non conformationally restricted control.