title: A new type of acyclic, achiral nucleoside analogue. How does it simulate nucleosides?
abstract: The new monomer 1 seems to be an excellent mimic of nucleosides with different sugar conformations (north, south, and envelope), because of the relatively free rotation around gamma, delta, and chi. The rotation around chi is primarily controlled by the repulsion between H6 and the two hydrogen atoms on C4' and not pi conjugation between the double bond and the nucleobase. A viable synthesis of the guanine monomer 8 is described.
authors.affiliation: Department of Chemistry, University of Copenhagen, The H.C. Orsted Institute, Copenhagen, Denmark.
authors.forename: Asger B
authors.initials: AB
authors.lastname: Petersen
authors.forename: Thomas
authors.initials: T
authors.lastname: Boesen
authors.forename: Otto
authors.initials: O
authors.lastname: Dahl
mesh_terms: D006147:Guanine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D007536:Isomerism; D008958:Models, Molecular; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D012399:Rotation
chemical_list: D009705:Nucleosides; D006147:Guanine