An unusual carbon–carbon bond cleavage reaction during phosphinothricin biosynthesis

Robert M. Cicchillo, Houjin Zhang, Joshua A. V. Blodgett, John T. Whitteck, Gongyong Li, Satish K. Nair (), Wilfred A. van der Donk () and William W. Metcalf ()
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Robert M. Cicchillo: University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA
Houjin Zhang: Institute for Genomic Biology,
Joshua A. V. Blodgett: University of Illinois at Urbana-Champaign, Urbana, Illinois 61802, USA
John T. Whitteck: University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA
Gongyong Li: University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA
Satish K. Nair: Institute for Genomic Biology,
Wilfred A. van der Donk: University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA
William W. Metcalf: Institute for Genomic Biology,

Nature, 2009, vol. 459, issue 7248, 871-874

Abstract: A novel carbon-carbon bond cleavage The phosphinothricin tripeptide (PTT) is a naturally occurring compound that contains a phosphorous-carbon bond. The biosynthesis of PTT involves the conversion of hydroxyethylphosphonate (HEP) to hydroxymethylphosphonate (HMP). The enzyme responsible for this chemical transformation (hydroxyethylphosphonate dioxygenase or HEPD) is a mononuclear non-haem iron(II)-dependent dioxygenase, and it catalyses the cleavage of a C(sp3)–C(sp3) bond. Here Robert Cicchillo and colleagues solve the X-ray crystal structure of HEPD and biochemically explore the mechanism of this remarkable transformation.

Date: 2009
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DOI: 10.1038/nature07972

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