title: Synthesis and duplex-stabilizing properties of fluorinated N-methanocarbathymidine analogues locked in the C3'-endo conformation.
abstract: The efficient synthesis, antiviral activity, and duplex-stabilizing properties of both isomers of the 2'-fluoro analogue of Northern methanocarbathymidine (N-MCT), 2 and 3, are reported. We show that 2'-F incorporation on the N-MCT scaffold has a strong stabilizing effect on duplex thermal stability.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095 (USA). jung@chem.ucla.edu.
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Timothy A
authors.initials: TA
authors.lastname: Dwight
authors.forename: Frederic
authors.initials: F
authors.lastname: Vigant
authors.forename: Michael E
authors.initials: ME
authors.lastname: Østergaard
authors.forename: Eric E
authors.initials: EE
authors.lastname: Swayze
authors.forename: Punit P
authors.initials: PP
authors.lastname: Seth
mesh_terms: D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D013936:Thymidine / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D009841:Oligonucleotides; C469995:(north)-methanocarbathymidine; D013936:Thymidine
keywords: asymmetric synthesis; diastereoselectivity; duplex thermal stability; fluorination; modified nucleosides