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Conformational and Chiral Selection of Oligonucleotides
Author(s) -
Froeyen Matheus,
Morvan François,
Vasseur JeanJacques,
Nielsen Peter,
Van Aerschot Arthur,
Rosemeyer Helmut,
Herdewijn Piet
Publication year - 2007
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200790065
Subject(s) - oligonucleotide , nucleic acid , dna , chemistry , homochirality , nucleic acid thermodynamics , stereochemistry , rna , enantiomer , biochemistry , gene , base sequence
In view of a better understanding of chiral selection of oligonucleotides, we have studied the hybridization of D ‐ and L ‐CNA (cyclohexane nucleic acids) and D ‐ and L ‐DNA, with chiral D ‐ β ‐homo‐DNA and achiral PNA (peptide nucleic acids). PNA hybridizes as well with D ‐DNA, L ‐DNA as with D ‐ β ‐homo‐DNA. The structure of the PNA⋅ D ‐ β ‐homo‐DNA complex is different from the PNA⋅DNA duplexes. D ‐CNA prefers D ‐DNA as hybridization partner, while L ‐CNA prefers D ‐ β ‐homo‐DNA as hybridization partner. The conformation of the enantiomeric oligonucleotides D ‐CNA and L ‐CNA in the supramolecular complex with D ‐DNA and D ‐ β ‐homo‐DNA, respectively, is different. These data may contribute to the confirmation of a hypothesis of the existence of achiral informative polymers as RNA predecessor, and to the understanding of homochirality of nucleic acids.