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Natural product biosynthesis

Tackling tunicamycin

Nature Chemistry volume 4, pages 520–521 (2012)Cite this article

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The tunicamycins, secondary metabolites of various Streptomyces species, are invaluable tools in glycobiology. It has now been shown that their biosynthesis involves an unusual exo-glycal intermediate produced by previously unknown short-chain dehydrogenase/reductase activity.

The tunicamycins (1), and closely related corynetoxins and streptoviridins, are nucleoside antibiotics with a range of useful biological activities. It was interest in the antiviral activity of these bacterial natural products that precipitated their isolation from Streptomyces lysosuperificus and chartreusis strains in the 1970s. They are now better known for their ability to inhibit the synthesis of peptidoglycan — a key component of the bacterial cell wall — and eukaryotic protein N-glycosylation (a ubiquitous process that is perhaps best appreciated for the role it plays in protein folding). Indeed, tunicamycin has become an important tool for the glycobiology and eukaryotic protein-production communities, where it is used to study the functional roles of protein N-glycosylation. As such, it is somewhat surprising that the biosynthesis of tunicamycin has only recently attracted the attention of chemical biologists1,2,3.

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Figure 1: Tunicamycin, tunicamine and the biosynthetic action of TunA — a protein in the short-chain dehydrogenase/reductase superfamily.

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  1. Ethan Goddard-Borger and Stephen Withers are in the Department of Chemistry at the University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1,

    Ethan D. Goddard-Borger & Stephen G. Withers

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  1. Ethan D. Goddard-Borger
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  2. Stephen G. Withers
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Correspondence to Stephen G. Withers.

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Goddard-Borger, E., Withers, S. Tackling tunicamycin. Nature Chem 4, 520–521 (2012). https://doi.org/10.1038/nchem.1391

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