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Biochemistry

The ylide has landed

Nature volume 498, pages 45–47 (2013)Cite this article

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The enzyme co-substrate SAM has long been known to have two chemically distinct roles. A study of the CmoA enzyme suggests that SAM has a third trick up its sleeve — it forms species known as ylides. See Letter p.123

Rarely has nature made such efficient use of a compound as it has of the biomolecule S-adenosylmethionine (SAM). SAM contains a positively charged sulphur atom known as a sulphonium group, which means that this molecule is often used as an electrophile — a polar species that is attracted to electron-rich centres. The compound also initiates a host of non-polar biochemical transformations that are mediated by free radicals1,2. But sulphonium groups have another ability that so far has not been observed in biochemical transformations: they can promote reactions by forming dipolar 'ylide' intermediates, which act as nucleophiles by reacting with electron-poor centres. In this issue, Kim et al.3 (page 123) report strong evidence that an ylide intermediate is formed from SAM in the biosynthesis of a modified nucleotide, 5-oxyacetyl uridineFootnote 1.

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Figure 1: An ylide biosynthetic intermediate.

Notes

  1. *This article and the paper under discussion3 were published online on 15 May 2013.

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Authors and Affiliations

  1. Bradley J. Landgraf and Squire J. Booker are in the Departments of Chemistry and of Biochemistry and Molecular Biology, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.,

    Bradley J. Landgraf & Squire J. Booker

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  1. Bradley J. Landgraf
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  2. Squire J. Booker
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Correspondence to Squire J. Booker.

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Landgraf, B., Booker, S. The ylide has landed. Nature 498, 45–47 (2013). https://doi.org/10.1038/nature12247

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