Heterologous Production of Fungal Maleidrides Reveals the Cryptic Cyclization Involved in their Biosynthesis

  • Katherine Williams
    Institute for Organic Chemistry Leibniz University of Hannover Schneiderberg 1B 30167 Germany
  • Agnieszka J. Szwalbe
    School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS UK
  • Nicholas P. Mulholland
    Syngenta Jealott's Hill Bracknell Berkshire RG42 6EY UK
  • Jason L. Vincent
    Syngenta Jealott's Hill Bracknell Berkshire RG42 6EY UK
  • Andrew M. Bailey
    School of Biological Sciences Bristol Life Sciences Building University of Bristol 24 Tyndall Ave Bristol BS8 1TH UK
  • Christine L. Willis
    School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS UK
  • Thomas J. Simpson
    School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS UK
  • Russell J. Cox
    Institute for Organic Chemistry Leibniz University of Hannover Schneiderberg 1B 30167 Germany

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<jats:title>Abstract</jats:title><jats:p>Fungal maleidrides are an important family of bioactive secondary metabolites that consist of 7, 8, or 9‐membered carbocycles with one or two fused maleic anhydride moieties. The biosynthesis of byssochlamic acid (a nonadride) and agnestadride A (a heptadride) was investigated through gene disruption and heterologous expression experiments. The results reveal that the precursors for cyclization are formed by an iterative highly reducing fungal polyketide synthase supported by a hydrolase, together with two citrate‐processing enzymes. The enigmatic ring formation is catalyzed by two proteins with homology to ketosteroid isomerases, and assisted by two proteins with homology to phosphatidylethanolamine‐binding proteins.</jats:p>

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