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)...

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Bibliographic Details
Published in:Nucleic Acids Symposium Series 2008, Vol.52 (1), p.275-276
Main Authors: Andersen, Charlotte, Sharma, Pawan K., Christensen, Mikkel S., Pedersen, Nikolai S., Nielsen, Poul
Format: Article
Language:English
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Summary: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.
ISSN:0261-3166
1746-8272
DOI:10.1093/nass/nrn139