Premium
Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids
Author(s) -
Lin HsiaoChing,
Chiou Grace,
Chooi YitHeng,
McMahon Travis C.,
Xu Wei,
Garg Neil K.,
Tang Yi
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201411297
Subject(s) - biosynthesis , tryptamine , indole test , gene cluster , computational biology , chemistry , tryptophan , stereochemistry , gene , biochemistry , biology , amino acid
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.