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    Nitrile Oxide/Alkyne Cycloadditions – A Credible Platform for Synthesis of Bioinspired Molecules by Metal-Free Molecular Clicking


    Heaney, Frances (2012) Nitrile Oxide/Alkyne Cycloadditions – A Credible Platform for Synthesis of Bioinspired Molecules by Metal-Free Molecular Clicking. European Journal of Organic Chemistry, 16. pp. 3043-3058. ISSN 1434-193X

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    Abstract

    The need for precise and flexible synthetic methodology to underpin modern research in chemical biology and materials science has fuelled a resurgence of interest in Huisgen 1,3-dipolar cycloaddition chemistry. Of late, the in vogue chemistry for the assembly of complex biological molecules and specialist materials has been the copper-catalysed azide alkyne cycloaddition (CuAAC) reaction. However, in certain circumstances aversion to the copper catalyst flaws this approach and alternatives have been sought. Click chemistry has developed beyond the original triazole-forming trick and azides are no longer the only dipoles pursued as click cycloaddition partners. This article reviews some of the complications of the CuAAC reaction and evaluates the potential of nitrile oxide/alkyne cycloaddition (NOAC) as a covalent conjugation tool. With a focus on applications in nucleic acid chemistry and materials science it presents the case for a prominent position for nitrile oxides in the catalyst-free bioconjugation toolbox.

    Item Type: Article
    Keywords: Bioorganic chemistry; Click chemistry; 1,3-Dipolar cycloaddition; Strain-promoted cycloaddition; Nucleic acids; Polymers; Alkynes;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 7742
    Identification Number: https://doi.org/10.1002/ejoc.201101823
    Depositing User: Dr. Frances Heaney
    Date Deposited: 13 Jan 2017 14:23
    Journal or Publication Title: European Journal of Organic Chemistry
    Publisher: Wiley
    Refereed: Yes
    Funders: Science Foundation Ireland (SFI)
    URI:

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