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Synthesis

Discriminating between carbohydrates

September 25, 2006 | A version of this story appeared in Volume 84, Issue 39

In recent years, scientists have created chemosensor systems inspired by the human tongue's combinatorial sensing approach. These lab sensors, though, still have a difficult time discriminating between molecules that are structurally very similar, such as carbohydrates containing only hydroxyl groups. Now, Young-Tae Chang and coworkers at New York University have used a new strategy that allows them to distinguish between 23 carbohydrates with 100% accuracy (Angew. Chem. Int. Ed., DOI: 10.1002/anie.200602055). The chemists take advantage of the fact that carbohydrates bind to boric acid or phenylboronic acid with unique strengths, a process that leads to diverse changes in pH. The pH changes resulting from each acid-carbohydrate reaction were determined by using a variety of organic pH indicator dyes and UV-visible spectroscopy. The data were used to construct a matrix of the colorimetric pH changes. Surprisingly, the researchers find that, using only six acid-indicator pairs, they can discriminate between the matrix patterns produced by all 23 carbohydrates, including mono-, di-, and trisaccharides. Practical application of this approach is under study.

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