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

Christian Wendeln, Ishwar Singh, Stefan Rinnen, Christian Schulz, Heinrich F Arlinghaus, Glenn A Burley, Bart Jan Ravoo

Research output: Contribution to journalArticle

35 Citations (Scopus)
245 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)2479-2484
Number of pages6
JournalChemical Science
Volume3
Issue number8
Early online date13 Jun 2012
DOIs
Publication statusPublished - 2012

Keywords

  • orthogonal
  • biochemical surface patterning
  • nitrile oxide cycloadditions

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