Sulfamide replacement of the phosphodiester linkage in dinucleotides: Synthesis and conformational analysis

Jason Micklefield, Kevin J. Fettes

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Dinucleotide analogues d(TnsnT) and d(TnsnA), in which the phosphodiester linkage of d(TpT) and d(TpA) is replaced by sulfamide [-NHSO2NH-], have been synthesised. Conformational analysis using 3J vicinal coupling constants shows that this modification results in a shift from a predominantly southern (C2'-endo) to northern (C3'-endo) ribose ring conformation. The effect of temperature and concentration changes on ribose conformation, reveals that the modified dinucleosides have a greater propensity to base stack intramolecularly, and in the case d(TnsnA), self-associate.
    Original languageEnglish
    Pages (from-to)2129-2142
    Number of pages13
    JournalTetrahedron
    Volume54
    Issue number10
    DOIs
    Publication statusPublished - 5 Mar 1998

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