title: Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids.
abstract: 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.
authors.affiliation: Department of Chemical and Biomolecular Engineering, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095 (USA).
authors.forename: Hsiao-Ching
authors.initials: HC
authors.lastname: Lin
authors.forename: Grace
authors.initials: G
authors.lastname: Chiou
authors.forename: Yit-Heng
authors.initials: YH
authors.lastname: Chooi
authors.forename: Travis C
authors.initials: TC
authors.lastname: McMahon
authors.forename: Wei
authors.initials: W
authors.lastname: Xu
authors.forename: Neil K
authors.initials: NK
authors.lastname: Garg
authors.forename: Yi
authors.initials: Y
authors.lastname: Tang
mesh_terms: D026121:Indole Alkaloids / Q000378:metabolism*
chemical_list: D026121:Indole Alkaloids
keywords: biosynthesis; communesins; gene deletion; indole alkaloids; structural elucidation