Synthesis and Pairing Properties of Oligonucleotides Containing 3-Hydroxy-4-hydroxymethyl-1-cyclohexanyl Nucleosides

Yuris Maurinsh, Helmut Rosemeyer, Robert Esnouf, Andrei Medvedovici, Jing Wang, Griet Ceulemans, Eveline Lescrinier, Chris Hendrix, Roger Busson, Pat Sandra,

Chemistry - A European Journal · 1999 · 56 citations · 0 references

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Abstract

Cyclohexanyl nucleic acid (CNA) represents a novel enantioselective Watson–Crick base-pairing system. Homochiral oligomers of equivalent chirality show antiparallel Watson–Crick pairing, while those of opposite sense do not. D-CNA hybridizes with natural nucleic acids, preferentially with RNA. A conformational change involving chair inversion is expected to occur upon duplex formation (A→B).