Journal
CHEMICAL SCIENCE
Volume 3, Issue 8, Pages 2479-2484Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc20555f
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Funding
- DFG [Ra1732/2]
- EPSRC [EP/E055095/1]
- Engineering and Physical Sciences Research Council [EP/E055095/1, EP/E055095/2] Funding Source: researchfish
- EPSRC [EP/E055095/2] Funding Source: UKRI
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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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