SYNTHESIS AND HYBRIDIZATION PROPERTIES OF AN OLIGONUCLEOTIDE ANALOG CONTAINING A GLUCOSE-DERIVED CONFORMATION-RESTRICTED RIBOSE MOIETY AND 2', 5' FORMACETAL LINKAGES

摘要

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. [References: 18]