Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids

H.C. Lin, G. Chiou, Heng Chooi, T.C. Mcmahon, W. Xu, N.K. Garg, Y. Tang

Research output: Contribution to journalArticle

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Abstract

© 2015 Wiley-VCH Verlag GmbH & Co. KGaA. 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.
Original languageEnglish
Pages (from-to)3004-3007
JournalAngewandte Chemie - International Edition
Volume54
DOIs
Publication statusPublished - 2015

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Indole Alkaloids
Penicillium
Biosynthetic Pathways
Gene Deletion
Multigene Family
Tryptophan
Molecular Biology
Pharmaceutical Preparations
tryptamine
aurantioclavine

Cite this

Lin, H.C. ; Chiou, G. ; Chooi, Heng ; Mcmahon, T.C. ; Xu, W. ; Garg, N.K. ; Tang, Y. / Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54. pp. 3004-3007.
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Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids. / Lin, H.C.; Chiou, G.; Chooi, Heng; Mcmahon, T.C.; Xu, W.; Garg, N.K.; Tang, Y.

In: Angewandte Chemie - International Edition, Vol. 54, 2015, p. 3004-3007.

Research output: Contribution to journalArticle

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