Discrimination of epimeric disaccharides by templated polymers

Efficient differentiation of epimeric disaccharides with templated poly(acrylates) is achieved. The rebinding event of the sugar epimers d-lactulose (1) and d-lactose (2) is based on shape recognition in unbuffered aqueous solution at neutral pH. A high-fidelity imprint of the disaccharide structures and functionality during material preparation has been demonstrated to be only achievable in a very narrow space around the immobilized binding site. Selectivity factors of 4.3 are observed in saturation competition experiments applying equimolar amounts of 1 and 2. Investigation of the coordination behavior of a copper(II) complex as functional monomer reveals defined 1:1 complex formation with both disaccharides in solution.