Synthesis of double-headed nucleosides with the additional nucleobase in the 5'-C-position.
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.
Andersen
Charlotte
C
Nucleic Acid Center, Department of Physics and Chemistry, University of Southern Denmark, 5230 Odense M, Denmark.
Sharma
Pawan K
PK
Christensen
Mikkel S
MS
Pedersen
Nikolai S
NS
Nielsen
Poul
P
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
D009705:Nucleosides; D009838:Oligodeoxyribonucleotides; D004247:DNA; D000241:Adenosine; D013936:Thymidine