title: 2'-Fluorination of tricyclo-DNA controls furanose conformation and increases RNA affinity.
abstract: The synthesis of 2'-fluoro tricyclo-DNA pyrimidine nucleosides with fluorine in the ribo-configuration and their incorporation into oligodeoxynucleotides was accomplished. Unlike the parent tc-T nucleoside, the 2'F-RNA-tc-T unit occurs in the 2'-exo conformation in the crystal. Specifically, F-RNA-tc-T was found to stabilize duplexes with RNA by +2 to +4 °C in Tm/mod. F-RNA-tc-nucleosides mix well with the DNA backbone and thus open up possibilities of using shorter and mixed-(DNA/tc-DNA) backbone oligonucleotides for therapeutic applications.
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
authors.forename: Alena
authors.initials: A
authors.lastname: Istrate
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
authors.forename: Michal
authors.initials: M
authors.lastname: Medvecky
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
authors.forename: Christian J
authors.initials: CJ
authors.lastname: Leumann
mesh_terms: D004247:DNA / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011743:Pyrimidines / Q000737:chemistry; D012313:RNA / Q000737:chemistry*
chemical_list: D005663:Furans; D011743:Pyrimidines; D005461:Fluorine; D012313:RNA; D004247:DNA; C030986:pyrimidine