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Synthetic chemistry

Sugaring vancomycin

Nature volume 397, pages 567–568 (1999)Cite this article

In a recent issue of Angewandte Chemie International Edition, Nicolaou and co-workers1 announced the total synthesis of the clinically important antibiotic vancomycin. The details of the final steps of this synthesis might turn out to be significant in the quest for modified antibiotics, which will, one hopes, perform better against serious clinical pathogens.

The discovery and exploitation of penicillin in the 1930s was a crucial advance in fighting bacterial infections, and was especially important during the Second World War. But, as early as the late 1950s, many strains of the bacterial pathogen Staphylococcus aureus were resistant to pencillin. The problem was initially kept at bay with the help of a semi-synthetic penicillin (methicillin). Butmethicillin-resistant S. aureus (MRSA) soon appeared and, by the 1980s, became resistant to the vast majority of available antibiotics2. Resistance arises from the process of Darwinian selection — antibiotics wipe out susceptible strains, but those chance mutants that possess antibiotic resistance survive.

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Figure 1: The structure of vancomycin with its constituent amino acids numbered 1 to 7.

References

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  1. the Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK

    Dudley H. Williams

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  1. Dudley H. Williams
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Williams, D. Sugaring vancomycin. Nature 397, 567–568 (1999). https://doi.org/10.1038/17489

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