title: Carbohydrate microarrays by microcontact printing.
abstract: This Article describes the preparation of carbohydrate microarrays by the immobilization of carbohydrates via microcontact printing (microCP) on glass and silicon substrates. To this end, diene-modified carbohydrates (galactose, glucose, mannose, lactose, and maltose) were printed on maleimide-terminated self-assembled monolayers (SAMs). A Diels-Alder reaction occurred exclusively in the contact area between stamp and substrate and resulted in a carbohydrate pattern on the substrate. It was found that cyclopentadiene-functionalized carbohydrates could be printed within minutes at room temperature, whereas furan-functionalized carbohydrates required long printing times and high temperatures. By successive printing, microstructured arrays of up to three different carbohydrates could be produced. Immobilization and patterning of the carbohydrates on the surfaces was investigated with contact angle measurements, X-ray photoelectron spectroscopy (XPS), time-of-flight secondary ion mass spectrometry (TOF-SIMS), and fluorescence microscopy. Furthermore, the lectins concanavalin A (ConA) and peanut agglutinin (PNA) bind to the microarrays, and the printed carbohydrates retain their characteristic selectivity toward these proteins.
authors.affiliation: Organic Chemistry Institute and Center for Nanotechnology, Westfalische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Wendeln
authors.forename: Andreas
authors.initials: A
authors.lastname: Heile
authors.forename: Heinrich F
authors.initials: HF
authors.lastname: Arlinghaus
authors.forename: Bart Jan
authors.initials: BJ
authors.lastname: Ravoo
mesh_terms: D002241:Carbohydrates / Q000032:analysis* / Q000737:chemistry*; D005898:Glass / Q000737:chemistry; D046228:Microarray Analysis / Q000379:methods*; D008856:Microscopy, Fluorescence; D008962:Models, Theoretical; D056951:Photoelectron Spectroscopy; D012825:Silicon / Q000737:chemistry; D018629:Spectrometry, Mass, Secondary Ion
chemical_list: D002241:Carbohydrates; D012825:Silicon