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Nucleic Acids Research, 2003, Vol. 31, No. 12 2975-2989
© 2003 Oxford University Press

Difference in conformational diversity between nucleic acids with a six-membered ‘sugar’ unit and natural ‘furanose’ nucleic acids

Eveline Lescrinier, Matheus Froeyen and Piet Herdewijn

Laboratory for Medicinal Chemistry, Rega Institute for Medical Research, Minderbroedersstraat 10, B-3000 Leuven, Belgium

*To whom correspondence should be addressed: Tel: +32 016337387; Fax: +32 016337340; Email: piet.herdewijn{at}rega.kuleuven.ac.be
In honour of Claude Hélène

Natural nucleic acids duplexes formed by Watson–Crick base pairing fold into right-handed helices that are classified in two families of secondary structures, i.e. the A- and B-form. For a long time, these A and B allomorphic nucleic acids have been considered as the ‘non plus ultra’ of double-stranded nucleic acids geometries with the only exception of Z-DNA, a left-handed helix that can be adopted by some DNA sequences. The five-membered furanose ring in the sugar–phosphate backbone of DNA and RNA is the underlying cause of this restriction in conformational diversity. A collection of new Watson–Crick duplexes have joined the ‘original’ nucleic acid double helixes at the moment the furanose sugar was replaced by different types of six-membered ring systems. The increase in this structural and conformational diversity originates from the rigid chair conformation of a saturated six-membered ring that determines the orientation of the ring substituents with respect to each other. The original A- and B-form oligonucleotide duplexes have expanded into a whole family of new structures with the potential for selective cross-communication in a parallel or antiparallel orientation, opening up a new world for information storage and for molecular recognition-directed self-organization.


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