Title: Structure of the fully modified left-handed cyclohexane nucleic acid sequence GT GTA CAC
Authors: Robeyns, Koen
Herdewijn, Piet
Van Meervelt, Luc # ×
Issue Date: 2008
Publisher: American Chemical Society
Series Title: Journal of the American Chemical Society vol:130 issue:6 pages:1979-1984
Abstract: CeNA oligonucleotides consist of a phosphorylated backbone where the deoxyribose sugars are replaced by cyclohexene moieties. The X-ray structure determination and analysis of a fully modified octamer sequence GTGTACAC, which is the first crystal structure of a carbocyclic-based nucleic acid, is presented. This particular sequence was built with left-handed building blocks and crystallizes as a lefthanded
double helix. The helix can be characterized as belonging to the (mirrored) A-type family. Crystallographic data were processed up to 1.53 Å, and the octamer sequence crystallizes in the space group R32. The sugar puckering is found to adopt the 3H2 half-chair conformation which mimics the C3'-endo conformation of the ribose sugar. The double helices stack on top of each other to form continuous
helices, and static disorder is observed due to this end-to-end stacking.
ISSN: 0002-7863
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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