Synthesis of 5-(pyridinyl and pyridiniumyl)-2'-deoxyuridine nucleosides: reversible electron traps for DNA.
The desire to produce reversible electron traps for direct, room temperature studies of excess electron transport in DNA duplexes and hairpins motivated our efforts first to link pyridines to 2'-deoxyuridine (pyridinyl-dU) and then to convert these new conjugates into pyridiniumyl-dU nucleosides. Base sensitivity studies presented here rule out general use of bipyridinediiumyl compounds, but show that pyridiniumyl compounds are suitable for use under the strand cleavage and base deprotection procedures required for automated solid-phase oligonucleotide synthesis. This paper presents the synthesis of four 5'-O-DMT-protected 5-(N-methylpyridiniumyl)-dU conjugates using either ethynyl or ethylenyl linkers to join the pyridiniumyl and dU subunits.
Gaballah
Samir T
ST
Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA.
Netzel
Thomas L
TL
D004247:DNA / Q000737:chemistry*; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D004579:Electron Transport; D006865:Hydrogenation; D009705:Nucleosides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013329:Structure-Activity Relationship
D009705:Nucleosides; D009943:Organophosphorus Compounds; D011725:Pyridines; C434331:phosphoramidite; D004247:DNA; C023666:pyridine; D003857:Deoxyuridine