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Synthetic chemistry

Glycosylation with a twist

Nature volume 437, pages 201–202 (2005)Cite this article

Nature has a whole battery of dedicated enzymes to make the complex links between sugar rings — how can synthetic chemists compete? An ingenious approach fills a big gap in the synthetic tool-kit.

Sugars can be linked together in a number of different ways to create chains. The resulting glycoside molecules have numerous biological functions, both by themselves and particularly when attached to proteins and lipids. The chemical reactions involved in making these molecules are formidable, and synthetic chemists have yet to find a set of robust chemical reactions that can generate the full complement of glycosidic linkages. In the Journal of the American Chemical Society, Boons and colleagues1 describe a cunning method that could fill a major gap in the chemical tool-kit required for the efficient synthesis of many glycosides that occur in nature.

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Figure 1: Configurations of glycosidic bonds using glucose as an example.
Figure 2: Sugar twist.

References

  1. Kim, J. -H., Yang, H., Park, J. & Boons, G. -J. J. Am. Chem. Soc. doi:10.1021/ja052548h (2005).

  2. Douglas, N. L. et al. J. Chem. Soc. Perkin Trans. 51–66 (1998).

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Authors and Affiliations

  1. School of Chemistry and the Manchester Interdisciplinary Biocentre, University of Manchester, Oxford Road, Manchester, M13 9PL, UK

    Sabine L. Flitsch

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  1. Sabine L. Flitsch
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Flitsch, S. Glycosylation with a twist. Nature 437, 201–202 (2005). https://doi.org/10.1038/437201a

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