Highly selective lipophilic diboronic acid that transports fructose as the trisdentate 2,3,6-β-d-fructofuranose ester |
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| Authors: | Scott P. DraffinPeter J. Duggan Sandhya A.M. DugganJens Chr. Norrild |
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| Affiliation: | a School of Chemistry, Monash University, Clayton, Melbourne, Vic. 3800, Australia
b Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark |
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| Abstract: | The transport of fructose and glucose through supported liquid membranes promoted by a tetrahedral shaped lipophilic monoboronic acid and diboronic acid, both based on a pentaerythritol core, has been studied. The diboronic acid gave a high fructose/glucose selectivity (7.7:1.0). The results of molecular modelling studies and 13C NMR experiments with uniformly labelled 13C-d-fructose suggest that the enhanced selectivity results from the formation of a trisdentate 2,3,6-β-d-fructofuranose diester within the membrane. Experimental evidence for a previously proposed macrocyclic d-fructopyranose diester formed with an o-phenylene linked diboronic acid has also been found. |
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| Keywords: | boronic acids membrane transport monosaccharides |
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