Structure of the fully modified left-handed cyclohexene nucleic acid sequence GTGTACAC

Journal of the American Chemical Society
Koen RobeynsLuc Van Meervelt

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 left-handed double helix. The helix can be characterized as belonging to the (mirrored) A-type family. Crystallographic data were processed up to 1.53 A, 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.

References

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Citations

Apr 13, 2010·Acta Crystallographica. Section F, Structural Biology and Crystallization Communications·Margriet OvaereLuc Van Meervelt
Sep 9, 2010·Acta Crystallographica. Section F, Structural Biology and Crystallization Communications·Koen RobeynsLuc Van Meervelt
Dec 18, 2015·Nucleic Acids Research·Irina AnosovaMartin Egli
Jun 12, 2014·Angewandte Chemie·Alberto Otero-de-la-RozaErin R Johnson
Jun 21, 2011·Artificial DNA, PNA & XNA·Koen RobeynsLuc Van Meervelt
Jan 1, 2012·Life·Victor Ostrovskii, Elena Kadyshevich
Jan 31, 2019·Physical Chemistry Chemical Physics : PCCP·Anuj Kumar, G Naresh Patwari
Sep 10, 2009·Chembiochem : a European Journal of Chemical Biology·Neil M Bell, Jason Micklefield
Jan 21, 2010·Chemistry & Biodiversity·Piet Herdewijn
May 28, 2011·Chemistry : a European Journal·Margriet OvaereLuc Van Meervelt
Mar 16, 2011·Chemistry & Biodiversity·Daniele D'AlonzoGiovanni Palumbo

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