Crystal structure of a B-form DNA duplex containing (L)-α-threofuranosyl (3′→2′) nucleosides: A four-carbon sugar is easily accommodated into the backbone of DNA

Christopher J. Wilds, Zdzislaw Wawrzak, Ramanarayanan Krishnamurthy, Albert Eschenmoser, Martin Egli*

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    57 Scopus citations

    Abstract

    (L)-α-Threofuranosyl-(3′→2′)-oligonucleotides (TNA) containing vicinally connected phosphodiester linkages undergo informational base pairing in an antiparallel strand orientation and are capable of cross-pairing with RNA and DNA. TNA is derived from a sugar containing only four carbon atoms and is one of the simplest potentially natural nucleic acid alternatives investigated thus far in the context of a chemical etiology of nucleic acid structure. Compared to DNA and RNA that contain six covalent bonds per repeating nucleotide unit, TNA contains only five. We have determined the atomic-resolution crystal structure of the B-form DNA duplex [d(CGCGAA)T*d(TCGCG)]2 containing a single (L)-α-threofuranosyl thymine (T*) per strand. In the modified duplex base stacking interactions are practically unchanged relative to the reference DNA structure. The orientations of the backbone at the TNA incorporation sites are slightly altered in order to accommodate fewer atoms and covalent bonds. The conformation of the threose is C4′-exo with the 2′- and 3′-substituents assuming quasi-diaxial orientation.

    Original languageEnglish (US)
    Pages (from-to)13716-13721
    Number of pages6
    JournalJournal of the American Chemical Society
    Volume124
    Issue number46
    DOIs
    StatePublished - Nov 20 2002

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)
    • Biochemistry
    • Colloid and Surface Chemistry

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