title: Synthesis of N2-alkyl-8-oxo-7,8-dihydro-2'-deoxyguanosine derivatives and effects of these modifications on RNA duplex stability.
abstract: N(2)-alkyl analogues of 8-oxo-7,8-dihydro-2'-deoxyguanosine (OG) were synthesized (alkyl = propyl, benzyl) via reductive amination of the protected OG nucleoside and incorporated into various positions of an RNA strand. Thermal stability studies of duplexes containing A or C opposite a single modified base revealed only moderate destabilization. Both OG as well as its N(2)-alkyl analogues can pair opposite A or C with nearly equal stability, potentially offering a new means of modulating RNA-protein interactions in the minor vs major grooves.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112-0850, United States.
authors.forename: Arunkumar
authors.initials: A
authors.lastname: Kannan
authors.forename: Cynthia J
authors.initials: CJ
authors.lastname: Burrows
mesh_terms: D000473:Alkanes / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D020137:Base Pair Mismatch; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012313:RNA / Q000737:chemistry*; D020871:RNA Stability
chemical_list: D000473:Alkanes; D012313:RNA; D003849:Deoxyguanosine