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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.
Original language | English |
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Pages (from-to) | 2479-2484 |
Number of pages | 6 |
Journal | Chemical Science |
Volume | 3 |
Issue number | 8 |
Early online date | 13 Jun 2012 |
DOIs | |
Publication status | Published - 2012 |
Keywords
- orthogonal
- biochemical surface patterning
- nitrile oxide cycloadditions
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Dive into the research topics of 'Orthogonal, metal-free surface modification by strain-promoted azide–alkyne and nitrile oxide–alkene/alkyne cycloadditions'. Together they form a unique fingerprint.Projects
- 1 Finished
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New Molecular Tools For The 21st Century: Molecular Design Of New DNA-Based Devices
EPSRC (Engineering and Physical Sciences Research Council)
1/04/12 → 31/03/13
Project: Research Fellowship