Genome mining approach for harnessing the cryptic gene cluster in Alternaria solani: Production of PKS-NRPS hybrid metabolite, didymellamide B

Takahiro Ugai, Atsushi Minami, Katsuya Gomi, Hideaki Oikawa

    Research output: Contribution to journalArticlepeer-review

    14 Citations (Scopus)

    Abstract

    Using a heterologous expression system in Aspergillus oryzae we characterized cryptic biosynthetic genes found in Alternaria solani. This system enabled the isolation of an antifungal metabolite, didymellamide B, which was previously not detected in the extract of the A. solani. The co-production and chemical transformation of didymellamide congeners enabled us to decipher the biosynthetic pathway of didymellamide B as follows: (1) formation of a linear polyketide chain with 3-acyltetramate, (2) oxidative ring expansion to yield a 2-pyridone skeleton, and (3) non-enzymatic endo-selective [4+2] cycloaddition to afford a trans-decalin. These results demonstrate the robustness and reliability of the A. oryzae expression system.

    Original languageEnglish
    Pages (from-to)2793-2796
    Number of pages4
    JournalTetrahedron Letters
    Volume57
    Issue number25
    DOIs
    Publication statusPublished - 2016 Jun 22

    Keywords

    • Didymellamide
    • Fungi
    • Heterologous expression
    • Natural product biosynthesis
    • Polyketide synthase

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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