An iterative in silico and modular synthetic approach to aqueous soluble tercyclic a-helix mimetics

Zelong Lim, Peter Duggan, Adam Meyer, Kellie Tuck

    Research output: Contribution to journalArticle

    5 Citations (Scopus)

    Abstract

    Tercyclic scaffolds, designed to have improved synthetic accessibility and aqueous solubility, were evaluated as structural α-helix mimetics by using an iterative in silico approach. The synthesis of these tercyclic scaffolds was accomplished using a modular synthetic approach by employing functionalised methoxyphenyl units which were readily manipulated to allow the introduction of various nitrogen-based heterocycles. The ability of these scaffolds to mimic the key i, i + 3 and i + 7 residues of a polyalanine α-helix was ratified by in silico studies, X-ray crystallographic and NOESY analysis, and their aqueous solubility was measured by a kinetic turbidimetric method.

    Original languageEnglish
    Pages (from-to)4432-4444
    Number of pages13
    JournalOrganic and Biomolecular Chemistry
    Volume12
    Issue number25
    DOIs
    Publication statusPublished - 7 Jul 2014

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