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Highly fructose selective transport promoted by boronic acids based on a pentaerythritol core
S P Draffin1, P J Duggan, S A Duggan
1Centre for Green Chemistry, School of Chemistry, P.O. Box 23, Monash University, Clayton, Melbourne, Victoria 3800, Australia.
Organic Letters
|March 27, 2001
Abstract:
We have designed and synthesized a highly lipophilic boronic acid (11) with a molecular shape that makes it much more effective at carrying sugars through organic membranes than a previously used steroidal boronic acid. The corresponding diboronic acid (12) was also found to transport fructose ahead of glucose with a very high selectivity (7.6:1.0). Modeling suggests that 12 is able to carry two fructose molecules at once in a complex stabilized through hydrogen bonding and ion pairing.