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Synthesis and Pairing Properties of Oligonucleotides Containing 3-Hydroxy-4-hydroxymethyl-1-cyclohexanyl Nucleosides
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1999
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Bioorganic ChemistryEngineeringMolecular BiologyOligonucleotides Containing 3-Hydroxy-4-hydroxymethyl-1-cyclohexanylOrganic ChemistryDna NanotechnologyNucleic Acid ChemistryChair InversionBiochemistryNatural Nucleic AcidsDiversity-oriented SynthesisOligonucleotideDna ReplicationAsymmetric CatalysisEnantioselective SynthesisStructural BiologyBiomolecular EngineeringCyclohexanyl Nucleic AcidNatural SciencesNucleic Acid Biochemistry
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).