Attach, remove, or replace: reversible surface functionalization using thiol-quinone methide photoclick chemistry.

Journal of the American Chemical Society
Selvanathan Arumugam, Vladimir V Popik

Abstract

A very facile reaction between photochemically generated o-naphthoquinone methides (oNQMs) and thiols is employed for reversible light-directed surface derivatization and patterning. A thiol-functionalized glass slide is covered with an aqueous solution of a substrate conjugated to 3-(hydroxymethyl)-2-naphthol (NQMP). Subsequent irradiation via shadow mask results in the efficient conversion of NQMP into reactive oNQM species in the exposed areas. The latter react with thiol groups on the surface, producing thioether links between the substrate and the surface. Unreacted oNQM groups are rapidly hydrated to regenerate NQMP. The short lifetime of oNQM in aqueous solution prevents its migration from the site of irradiation, thus allowing for the spatial control of the surface derivatization. A two-step procedure was employed for protein patterning: photobiotinylation of the surface with an NQMP-biotin conjugate followed by staining with FITC-avidin. The orthogonality of oNQM-thiol and azide click chemistry allowed for the development of a sequential click strategy, which might be useful for the immobilization of light-sensitive compounds. The thioether linkage produced by the reaction of oNQM and a thiol is stable under ambient co...Continue Reading

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Nov 7, 2012·Journal of the American Chemical Society·Lanti YangPascal Jonkheijm
Mar 26, 2013·Journal of the American Chemical Society·Qiang LiXiaoguang Lei
Apr 26, 2014·Chemical Science·Selvanathan ArumugamVladimir V Popik
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