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)

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.
LanguageEnglish
Pages2479-2484
Number of pages6
JournalChemical Science
Volume3
Issue number8
Early online date13 Jun 2012
DOIs
Publication statusPublished - 2012

Fingerprint

Nitriles
Alkynes
Azides
Cycloaddition
Alkenes
Oxides
Surface treatment
Metals
Oximes
Printing
Biomolecules
Self assembled monolayers
Oxidation
Substrates

Keywords

  • orthogonal
  • biochemical surface patterning
  • nitrile oxide cycloadditions

Cite this

Wendeln, Christian ; Singh, Ishwar ; Rinnen, Stefan ; Schulz, Christian ; Arlinghaus, Heinrich F ; Burley, Glenn A ; Ravoo, Bart Jan. / Orthogonal, metal-free surface modification by strain-promoted azide–alkyne and nitrile oxide–alkene/alkyne cycloadditions. In: Chemical Science. 2012 ; Vol. 3, No. 8. pp. 2479-2484.
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Orthogonal, metal-free surface modification by strain-promoted azide–alkyne and nitrile oxide–alkene/alkyne cycloadditions. / Wendeln, Christian; Singh, Ishwar; Rinnen, Stefan; Schulz, Christian; Arlinghaus, Heinrich F; Burley, Glenn A; Ravoo, Bart Jan.

In: Chemical Science, Vol. 3, No. 8, 2012, p. 2479-2484.

Research output: Contribution to journalArticle

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T1 - Orthogonal, metal-free surface modification by strain-promoted azide–alkyne and nitrile oxide–alkene/alkyne cycloadditions

AU - Wendeln, Christian

AU - Singh, Ishwar

AU - Rinnen, Stefan

AU - Schulz, Christian

AU - Arlinghaus, Heinrich F

AU - Burley, Glenn A

AU - Ravoo, Bart Jan

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AB - 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.

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