Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids1. (8th January 2015)

• Record Type: Journal Article
• Authors: Lin, Hsiao‐Ching; Chiou, Grace; Chooi, Yit‐Heng; McMahon, Travis C.; Xu, Wei; Garg, Neil K.; Tang, Yi
• Is Part Of: Angewandte Chemie. Volume 127:Number 10(2015)
• Page Start: 3047
• Page End: 3050
• Publication Date: 2015-01-08
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201411297
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The communesins are a prominent class of indole alkaloids isolated from <italic>Penicillium</italic> 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 (<italic>cns</italic>) biosynthetic gene cluster from <italic>Penicillium expansum</italic>. We confirmed that communesin is biosynthesized by the coupling of tryptamine and aurantioclavine, two building blocks derived from <sc>L</sc>‐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.</p> </abstract>