2H0N

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

Summary for 2H0N

• Entry DOI: 10.2210/pdb2h0n/pdb
• Descriptor: 5'-(*(XGL)P*(XTL)P*(XGL)P*(XTL)P*(XAL)P*(XCL)P*(XAL)P*(XCL)-Phosphate)-3', DIHYDROGENPHOSPHATE ION (3 entities in total)
• Functional Keywords: cyclohexene nucleic acid, dna analogue, left-handed, double helix, dna
• Total number of polymer chains: 2
• Total formula weight: 5207.82

Authors

Robeyns, K.,Van Meervelt, L. (deposition date: 2006-05-15, release date: 2007-04-24, Last modification date: 2024-04-03)

Primary citation

Robeyns, K.,Herdewijn, P.,Van Meervelt, L.
Structure of the fully modified left-handed cyclohexene nucleic acid sequence GTGTACAC.
J.Am.Chem.Soc., 130:1979-1984, 2008

PubMed 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.

PubMed: 18198873
DOI: 10.1021/ja077313f

Experimental method

X-RAY DIFFRACTION (1.53 Å)