The cyclohexane nucleosides with a 1,4-relationship between nucleoside base and hydroxymethyl moiety were synthesized using a conjugated addition reaction of the nucleobases to ethyl 1,3-cyclohexadiene-1-carboxylate and hydroboration of the cyclohexenyl precursor. The lack of antiviral activity of the compounds was correlated with the conformation of these nucleosides as deduced from NMR and X-ray analysis.

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nucleic acids are RNA-selective. l-CNA hybridizes either very weakly or not at all with natural nucleic acids, and the nature of this association is not clear. This study of CNAs leads us to hypothesize that a) the conformation of a single nucleoside analogue may be different from its conformation in an oligonucleotide and b) the conformational stress of a nucleotide analogue incorporated in an oligomer may contribute to the sequence-dependent thermal stability of oligonucleotide complexes.