Noncovalent fluorous interactions for the synthesis of carbohydrate microarrays

A surface patterning method based on noncovalent immobilization of fluorous-tagged sugars on fluorous-derivatized glass slides allows the facile fabrication of carbohydrate microarrays. To expand the scope of these arrays, the first syntheses are reported of arabinose, rhamnose, lactose, maltose, and glucosamine tagged with a single C8F17-tail for ease of purification as well as array formation. Screening of these carbohydrate microarrays against lectins from Triticum vulgaris (WGA) and Arachis hypogaea (PNA) demonstrate that the noncovalent fluorous–fluorous interaction is sufficient to retain not only mono- but also disaccharides under the biological assay conditions.

The first syntheses are reported of arabinose, rhamnose, lactose, maltose, and glucosamine tagged with a single C8F17-tail for ease of purification as well as for facile array formation. Screening of these carbohydrate microarrays against two lectins demonstrates that the noncovalent fluorous–fluorous interaction is sufficient to retain both mono- and disaccharides. Figure optionsDownload as PowerPoint slide