title: A set of nonpolar thymidine nucleoside analogues with gradually increasing size.
abstract: [structure: see text] We describe a series of nonpolar nucleoside analogues having similar shapes and gradually increasing size. The structure of the nucleobase thymine was mimicked with toluene derivatives, replacing O2/O4 with hydrogen, fluorine, chlorine, bromine, and iodine. Glycosidic bonds were formed by reactions of lithiated 2,4-dihalotoluenes with a deoxyribonolactone derivative. Structural analysis by NMR showed similar conformations across the series. The compounds are useful for study of the biological recognition of nucleotides and nucleic acids.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
authors.forename: Tae Woo
authors.initials: TW
authors.lastname: Kim
authors.forename: Eric T
authors.initials: ET
authors.lastname: Kool
mesh_terms: D018360:Crystallography, X-Ray; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D008968:Molecular Conformation; D009696:Nucleic Acids / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis*; D009711:Nucleotides / Q000737:chemistry; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D014050:Toluene / Q000737:chemistry
chemical_list: D006846:Hydrocarbons, Halogenated; D007783:Lactones; D009696:Nucleic Acids; D009705:Nucleosides; D009711:Nucleotides; C057020:ribonolactone; D014050:Toluene; D012266:Ribose; D013936:Thymidine