A novel class of conformationally restricted oligonucleotide analogues: synthesis of 2′,3′-bridged monomers and RNA-selective hybridisation

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Poul Nielsen, Henrik M. Pfundheller and Jesper Wengel


Abstract

A novel 2′,3′-bicyclic nucleoside 5 has been synthesised and incorporated into oligonucleotide analogues resulting in strong and selective binding to an RNA complement.


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