The first example of a positive, homotropic system in aqueous saccharide-binding has been achieved using a Ce(IV) bis(porphyrinate) double decker scaffold bearing two pairs of boronic acid groups (compound 2). In this system, the binding of the first guest (1:2 saccharide/boronic acid complex) suppresses the rotational freedom of the two porphyrin planes, which facilitates the binding of the second guest. As a result, two pairs of boronic acid groups in 2 can autoacceleratively bind these guests and yield CD-active species. The analyses of CD intensity-guest concentration plots according to the Hill equation resulted in K=3.7x104 M-2 and n=2.0 for D- fructose and K=9.6x105 M-2 and n=1.6 for D-glucose. The present system which is in action even in aqueous media is widely applicable to allosteric control of drug release, catalytic reaction, information transduction, etc. of saccharide-containing guest molecules. (C) 2000 Elsevier Science Ltd.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry