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Orthogonal, metal-free surface modification by strain-promoted azide–alkyne and nitrile oxide–alkene/alkyne cycloadditions

Wendeln, Christian and Singh, Ishwar and Rinnen, Stefan and Schulz, Christian and Arlinghaus, Heinrich F and Burley, Glenn A and Ravoo, Bart Jan (2012) Orthogonal, metal-free surface modification by strain-promoted azide–alkyne and nitrile oxide–alkene/alkyne cycloadditions. Chemical Science, 3 (8). pp. 2479-2484. ISSN 2041-6520

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    Abstract

    In this article we present a fast and efficient methodology for biochemical surface patterning under extremely mild conditions. Micropatterned azide/benzaldoxime-surfaces were prepared by microcontact printing of a heterobifunctional cyclooctyne oxime linker on azide-terminated self-assembled monolayers (SAMs). Strain-promoted azide–alkyne cycloaddition (SPAAC) in combination with microcontact printing allows fast and effective surface patterning. The resulting bifunctional azide/oxime substrates could successfully be used for metal-free, orthogonal immobilization of various biomolecules by 1,3-dipolar cycloadditions at room temperature. Azide-decorated areas were modified by reaction with a cyclooctyne-conjugate using SPAAC, while benzaldoxime-decorated areas were activated by in situ oxidation to the reactive nitrile oxides and subsequent nitrile oxide cycloaddition with alkene- and alkyne-functionalized bioconjugates. In addition, orthogonal double immobilization was achieved by consecutive and independent SPAAC and nitrile oxide cycloadditions.

    Item type: Article
    ID code: 40944
    Keywords: orthogonal, biochemical surface patterning, nitrile oxide cycloadditions, Chemistry, Chemistry(all)
    Subjects: Science > Chemistry
    Department: Faculty of Science > Pure and Applied Chemistry
    Technology and Innovation Centre > Bionanotechnology
    Related URLs:
      Depositing user: Pure Administrator
      Date Deposited: 21 Aug 2012 16:18
      Last modified: 12 Apr 2014 07:30
      URI: http://strathprints.strath.ac.uk/id/eprint/40944

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