Synthesis and properties of water-soluble cyclophanes bearing saccharide residues

ORGN 747

Osamu Hayashida, ohaya@ms.ifoc.kyushu-u.ac.jp and Itaru Hamachi. Institute for Materials Chemistry and Engineering, Kyushu University, Hakozaki 6-10-1, Higashi-ku, Fukuoka, 812-8581, Japan
In this contribution we present the synthesis of water-soluble hosts composed of a tetraaza[6.1.6.1]paracyclophane and four branches with a terminal glucose or galactose residue. The cyclophane moiety provides a cavity for guest-binding, while terminal glucoside moieties act as a tag directed toward carbohydrate-binding proteins (lectins). The saccharide cyclophane was selectively bound to the lectin, which was readily monitored by a visible turbidity of the solution due to a cross-linking agglutination of these components. The guest-binding ability of the saccharide cyclophane for hydrophobic guests such as amine-reactive fluorescent dye and its saccharide-directed chemical modification toward a lectin were examined from a viewpoint of fluorescent biosensor. The synthesis and characterization of cyclophanes having other kind of saccharide residues will also be presented.