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Boronic acids for proteoglycan targeting
Synthesis of libraries targeting carbohydrates: The selective recognition of carbohydrates under physiological conditions stands as one of the biggest challenges of chemical biology. In this context, boronic acids are among the most promising candidates for specific recognition of carbohydrates in water. However, this approach has severe limitations: most boronic acids have not yet been demonstrated to bind to nonreducing sugars and glycosides, which account for the large majority of oligosaccharides found in the form of cell-surface glycoconjugates. Moreover, many of the currently established standard boronic acids for the recognition of simple carbohydrates tend to have limited solubility in aqueous solutions. Notable exceptions are ortho-functionalized phenylboronic acids, which have been recently shown to bind glycosidic structures selectively. For the detection of cancer specific cell surface proteoglycanes we would therefore like to use phenylboronates as scaffolds and functionalize them to overcome the above mentioned drawbacks and make them amenable to tumour targeting.
This project involves the solid phase synthesis of phenylboronic acids and their functionalization with different moieties such as sugars, peptides and unnatural structures. Split-and-mix combinatorial approaches will be used to create small libraries on solid support.
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17.12.2007 11:27
