CARB 18 |
| Bis(boronic acids) have been widely used in the development of chemosensors for sugars, most importantly glucose. We have previously reported that bis(boronates) have an even higher affinity for bis(α-hydroxycarboxylates) such as tartrate than for simple bis(diols) like erythritol.[1] We will look at the design of novel boronate-based receptors for α-hydroxyacids and inositols[2], an important class of cell-signalling molecules. The affinity of boric and boronic acids for α-hydroxycarboxylates has also been shown to catalyze esterification of these species and this reaction is applicable to carbohydrates.[3] [1] Gray, Jr., C. W.; Houston, T. A. J. Org. Chem. 2002, 67, 5426. [2] Gray, Jr., C. W.; Johnson, Jr., L. L.; Walker, B. T.; Sleevi, M.; Campbell, A. S.; Plourde, R.; Houston, T. A. Bioorg. Med. Chem. Lett. 2005, 15, 5416. [3] Houston, T. A.; Wilkinson, B. L.; Blanchfield, J. T. Org. Lett. 2004, 6, 679. |
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Carbohydrate Recognition Mechanisms and Applications
9:00 AM-12:15 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- B409, Oral
Division of Carbohydrate Chemistry |