Issue Date: July 16, 2007
Amended Route To Odd Natural Product
A revised view of how an unusual phosphinic acid-containing natural product is put together has emerged from a study by Neil L. Kelleher, Wilfred A. van der Donk, William W. Metcalf, and coworkers at the University of Illinois, Urbana-Champaign (Nat. Chem. Biol., DOI: 10.1038/nchembio.2007.9). The antibiotic and potent herbicide phosphinothricin tripeptide (PTT, shown) is the only known naturally occurring compound containing a carbon-phosphorus-carbon bond. Nature's route to this compound, which was first isolated in 1972 from Streptomyces bacteria, has therefore been the subject of intense scrutiny. A number of enzymes needed to make PTT have been identified, and armed with this knowledge, the researchers set out to characterize the natural product's complete biosynthetic pathway. By using 31P NMR spectroscopy, mass spectrometry, and enzyme mutagenesis, they identified two overlooked intermediates. Their revised route to PTT includes several previously unknown enzyme-catalyzed transformations, including a highly unusual method of carbon-bond cleavage.
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