title: Synthesis of double-headed nucleosides with the additional nucleobase in the 5'-C-position.
abstract: Three analogues of double-headed nucleosides with the additional nucleobase in the 5'(S)-C-position have been synthesised. A thymine has been attached through a methylene or an ethylene linker and an adenine through a methylene linker. Thermal hybridisation studies indicate that this 5' (S)-C-position is ideal for placing the additional base in the minor groove and obtain specific interstrand stacking effects in a (-3)-zipper arrangement. However, this specific interaction is decreasing when elongating the linker from a methylene to an ethylene linker. The successful syntheses of the two nucleoside analogues with thymine in the 5'-C-position as well as different approaches towards a corresponding adenine analogue are reported.
authors.affiliation: Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Andersen
authors.forename: Pawan K
authors.initials: PK
authors.lastname: Sharma
authors.forename: Mikkel S
authors.initials: MS
authors.lastname: Christensen
authors.forename: Nikolai S
authors.initials: NS
authors.lastname: Pedersen
authors.forename: Poul
authors.initials: P
authors.lastname: Nielsen
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D004247:DNA; D000241:Adenosine; D013936:Thymidine