A set of nonpolar thymidine nucleoside analogues with gradually increasing size.
[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.
Kim
Tae Woo
TW
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA.
Kool
Eric T
ET
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
D006846:Hydrocarbons, Halogenated; D007783:Lactones; D009696:Nucleic Acids; D009705:Nucleosides; D009711:Nucleotides; C057020:ribonolactone; D014050:Toluene; D012266:Ribose; D013936:Thymidine