The Interaction of Oligosaccharide-Branched Cyclodextrins with Immobilized Concanavalin A

New oligosaccharide-branched β-cyclodextrins (10–12) having various oligosaccharides in the primary (C6) hydroxyl group of β-cyclodextrin (CD) were synthesized. Oligosaccharides were converted to lactones at the reducing end, which was connected with 6-monoamino-β-CD forming an amide bond. They were examined for the interaction with the immobilized concanavalin A (Con A) and compared to available 6-O-glucosyl and maltosyl CDs (1–9). For the analysis of the interaction between Con A immobilized on an aminosilane-hydrogel surface and various oligosaccharides, a biosensor of the FISONS IAsys apparatus based on a resonant mirror detector (RMD) was used. As a result, it interacted with immobilized Con A and both maltosyl-β-CD (6) and maltosyl-γ-CD (9), and glucosyl-glucono-amide-β-CD (10) with association constants, Ka, of 134, 833, and 8570 M−1, respectively. Con A showed the distinct sugar chain recognition to glucosyl-glucono-amide-β-CD (10). The other oligosaccharide-branched CDs showed rather complicated and obscure interaction.