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An unusual carbon–carbon bond cleavage reaction during phosphinothricin biosynthesis

Author

Listed:
  • Robert M. Cicchillo

    (University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA
    Institute for Genomic Biology,
    Howard Hughes Medical Institute,)

  • Houjin Zhang

    (Institute for Genomic Biology,
    and)

  • 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
    Institute for Genomic Biology,)

  • Gongyong Li

    (University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA)

  • Satish K. Nair

    (Institute for Genomic Biology,
    and)

  • Wilfred A. van der Donk

    (University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA
    Institute for Genomic Biology,
    Howard Hughes Medical Institute,
    and)

  • William W. Metcalf

    (Institute for Genomic Biology,
    University of Illinois at Urbana-Champaign, Urbana, Illinois 61802, USA)

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.

Suggested Citation

  • Robert M. Cicchillo & Houjin Zhang & Joshua A. V. Blodgett & John T. Whitteck & Gongyong Li & Satish K. Nair & Wilfred A. van der Donk & William W. Metcalf, 2009. "An unusual carbon–carbon bond cleavage reaction during phosphinothricin biosynthesis," Nature, Nature, vol. 459(7248), pages 871-874, June.
    • Handle: RePEc:nat:nature:v:459:y:2009:i:7248:d:10.1038_nature07972
    DOI: 10.1038/nature07972
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    Cited by:

    1. Leixia Chu & Xiaoxia Luo & Taoting Zhu & Yingying Cao & Lili Zhang & Zixin Deng & Jiangtao Gao, 2022. "Harnessing phosphonate antibiotics argolaphos biosynthesis enables a synthetic biology-based green synthesis of glyphosate," Nature Communications, Nature, vol. 13(1), pages 1-16, December.

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