Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids

Details

• Alternative Title:
  Angew Chem Int Ed Engl
• Personal Author:
  Lin, Hsiao-Ching ; Chiou, Grace ; Chooi, Yit-Heng ; McMahon, Travis C. ; Xu, Wei ; Garg, Neil K. ; Tang, Yi
• 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.
• Subjects:
  Indole Alkaloids
• Keywords:
  Alkaloids Biosynthesis Communesins
• Source:
  Angew Chem Int Ed Engl. 54(10):3004-3007
• Pubmed ID:
  25571861
• Pubmed Central ID:
  PMC4409825
• Document Type:
  Journal Article
• Funding:
  S10RR025631/RR/NCRR NIH HHSUnited States/ ; 1R56AI101141/AI/NIAID NIH HHSUnited States/ ; DP1 GM106413/GM/NIGMS NIH HHSUnited States/ ; S10 RR025631/RR/NCRR NIH HHSUnited States/ ; 1DP1GM106413/DP/NCCDPHP CDC HHSUnited States/ ; R56 AI101141/AI/NIAID NIH HHSUnited States/
• Volume:
  54
• Issue:
  10
• Collection(s):
  CDC Public Access
• Main Document Checksum:
  urn:sha256:2e323717f40fd48045b352a2844726e834f12c99024107c7bbadd477e4b6a031
• Download URL:
  https://stacks.cdc.gov/view/cdc/30652/cdc_30652_DS1.pdf
• File Type:
  [PDF - 1.42 MB ]