Title: Influence of the incorporation of a cyclohexenyl nucleic acid residue into the sequence d(CGCGAATTCGGCG)
Authors: Robeyns, Koen
Herdewijn, Piet
Van Meervelt, Luc # ×
Issue Date: Mar-2008
Publisher: Oxford University Press
Series Title: Nucleic acids research vol:36 issue:5 pages:1407-1414
Abstract: Cyclohexene nucleic acids (CeNA), which are characterized by the presence of a cyclohexene moiety instead of a natural (deoxy)ribose sugar, are known to increase the thermal and enzymatic stability when incorporated in RNA oligonucleotides. As it has been demonstrated that even a single cyclohexenyl nucleoside, when incorporated in an oligonucleotide, can have a profound effect on the biological activity of the oligonucleotide, further research is warranted to study the complex of such oligonucleotides with target proteins. In order to analyse the influence of CeNA residues onto the helix conformation and hydration of natural nucleic acid structures, a cyclohexenyl-adenine building block (xAr) was incorporated into the Dickerson sequence CGCGA(xAr)TTCGCG. The crystal structure of this sequence determined to a resolution of 1.90 Å. The global helix belongs to the B-type family and shows a water spine, which is partially broken up by the apolar cyclohexene residue. The cyclohexene ring adopts the 2E-conformation allowing a better incorporation of the residue in the dodecamer sequence. The crystal packing is stabilized by cobalt hexamine residues and belongs to space group P2221, never before reported for nucleic acids.
ISSN: 0305-1048
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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