title: Synthesis, duplex stabilization and structural properties of a fluorinated carbocyclic LNA analogue.
abstract: DNA oligonucleotides modified with nucleoside monomers which have an electron withdrawing group (EWG) at the 2'-position of the furanose ring form more stable duplexes with complementary RNA as compared to unmodified DNA. Here we show that an anti-periplanar orientation of the nucleobase and the 2'-EWG is important for optimal duplex stabilization even for nucleic acid analogues with conformationally locked furanose rings.
authors.affiliation: Department of Medicinal Chemistry, Isis Pharmaceuticals, 2855 Gazelle Court, Carlsbad, CA 92010, USA. pseth@isisph.com
authors.forename: Punit P
authors.initials: PP
authors.lastname: Seth
authors.forename: Pradeep S
authors.initials: PS
authors.lastname: Pallan
authors.forename: Eric E
authors.initials: EE
authors.lastname: Swayze
authors.forename: Martin
authors.initials: M
authors.lastname: Egli
mesh_terms: D001483:Base Sequence; D060326:Chemistry Techniques, Synthetic; D054879:Halogenation; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000235:genetics
chemical_list: D009841:Oligonucleotides; C477371:locked nucleic acid