title: Rapid preparation of multifunctional surfaces for orthogonal ligation by microcontact chemistry.
abstract: Microcontact chemistry has been applied to patterned glass and silicon substrates by successive reaction of unprotected and monoprotected heterobifunctional linkers with alkene-terminated self-assembled monolayers (SAMs) to produce bi-, tri-, and tetrafunctional surfaces. Photochemical microcontact printing of an azide thiol linker followed by immobilization of an acid thiol linker on an undecenyl-terminated SAM results in a well-defined, micropatterned surface with terminal azide, acid, and alkene groups. Biologically relevant molecules (biotin, carbohydrates) have been selectively attached to the surface by means of orthogonal ligation chemistry, and the resulting microarrays display selective binding to fluorescently labeled proteins. An orthogonally addressable, tetrafunctional surface (azide, acid, alkene, and amine) can be prepared by an additional printing step of a tert-butyloxycarbonyl (Boc)-protected alkyne amine linker on the azide structures by using the copper(I)-catalyzed azide-alkyne Huisgen cycloaddition and subsequent removal of the protective group.
authors.affiliation: Organisch Chemisches Institut and Center for Nanotechnology (CeNTech), Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Wendeln
authors.forename: Stefan
authors.initials: S
authors.lastname: Rinnen
authors.forename: Christian
authors.initials: C
authors.lastname: Schulz
authors.forename: Tobias
authors.initials: T
authors.lastname: Kaufmann
authors.forename: Heinrich F
authors.initials: HF
authors.lastname: Arlinghaus
authors.forename: Bart Jan
authors.initials: BJ
authors.lastname: Ravoo
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry; D057930:Click Chemistry; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D011506:Proteins / Q000737:chemistry; D013499:Surface Properties
chemical_list: D000475:Alkenes; D002241:Carbohydrates; D017646:Organosilicon Compounds; D011506:Proteins