Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 10, Pages 3004-3007Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201411297
Keywords
biosynthesis; communesins; gene deletion; indole alkaloids; structural elucidation
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Funding
- National Science Council of Taiwan [102-2917-I-564-008]
- NSF Graduate Research Fellowship [DGE-0707424]
- NIH grants [1DP1GM106413, 1R56AI101141]
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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.
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