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Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids
Filetype[PDF - 1.42 MB]


Details:
  • Pubmed ID:
    25571861
  • Pubmed Central ID:
    PMC4409825
  • Funding:
    1DP1GM106413/DP/NCCDPHP CDC HHS/United States
    1R56AI101141/AI/NIAID NIH HHS/United States
    DP1 GM106413/GM/NIGMS NIH HHS/United States
    R56 AI101141/AI/NIAID NIH HHS/United States
    S10 RR025631/RR/NCRR NIH HHS/United States
    S10RR025631/RR/NCRR NIH HHS/United States
  • Document Type:
  • Collection(s):
  • Description:
    The communesins are a prominent class of indole alkaloids isolated from Penicillium species. Owing to their daunting structural framework and potential as pharmaceuticals, communesins have inspired numerous synthetic studies. However, the genetic and biochemical basis of communesin biosynthesis has remained unexplored. Herein, we report the identification and characterization of the communesin (cns) biosynthetic gene cluster from Penicillium expansum. We confirmed that communesin is biosynthesized by the coupling of tryptamine and aurantioclavine, two building blocks derived from L-tryptophan. The postmodification steps were mapped by targeted-gene-deletion experiments and the structural elucidation of intermediates and new analogues. Our studies set the stage for the biochemical characterization of communesin biosynthesis. This knowledge will aid our understanding of how nature generates remarkable structural complexity from simple precursors.