An experimental strategy towards optimising directed biosynthesis of communesin analogues by Penicillium marinum in submerged fermentation

Wigley, Lucy J.; Perry, David A.; Mantle, Peter G.

doi:10.1016/j.mycres.2007.09.003

Cited by 15 publications

(11 citation statements)

References 7 publications

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“…In contrast, the biosynthetic pathway of the communesins has remained unexplored since their isolation except for preliminary feeding experiments, which showed that the communesin core is assembled from two indole precursors derived from tryptophan 2e. 4 Stoltz and co‐workers proposed several biosynthetic possibilities, all of which involve the coupling of tryptamine and aurantioclavine ( 10 ) as a key step in the construction of the core structure 5. To understand how nature generates the structural complexity seen in the communesins, we set out to characterize the responsible alkaloid biosynthetic gene cluster.…”

Section: Methodsmentioning

confidence: 99%

“…We reasoned that the N ‐hexadienyl acyl chain in 2 must be derived from a highly reducing PKS, whereas the isoprenoid unit on the indoline must be installed by an enzyme homologous to 4‐dimethylallyl tryptophan synthase (DMATS). Furthermore, precursor feeding studies showed that one equivalent of 6‐fluorotryptamine can be incorporated into 1 and 2 ,2e, 4 thus suggesting the likely presence of a tryptophan decarboxylase (TDC). We therefore searched for a gene cluster that contained a PKS, DMATS, and TDC in close proximity to each other in the P. expansum genome.…”

Section: Methodsmentioning

confidence: 99%

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Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids

et al. 2015

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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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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids

et al. 2015

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“…It remained unclear how 32 should then be transformed into 3 . In 2008, the authors added the comment that aurantioclavine ( 21 ) could well be a precursor in fungal communesin biosynthesis,5b as suggested by Stoltz and co‐workers2a (Scheme ).…”

Section: Biogenetic Considerationsmentioning

confidence: 99%

It All Began with an Error: The Nomofungin/Communesin Story

2008

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The communesin/nomofungin/perophoramidine story is an impressive example of how biogenetic considerations can lead to the correction of structural misassignments and inspire synthetic chemists with new, fruitful ideas. Intensive studies by a number of research groups culminated in the total synthesis of perophoramidine by the Funk research group in 2004. In 2007, Qin and co-workers completed the first total synthesis of a communesin.

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“…Es blieb unklar, wie sich 32 in 3 umwandeln sollte. Im Jahr 2008 fügten die Autoren noch die Bemerkung an,5b Aurantioclavin ( 21 ) könne sehr wohl bei der im Pilz stattfindenden Communesin‐Biosynthese als Ausgangsmaterial dienen, ganz im Einklang mit dem Vorschlag von Stoltz (Schema ).…”

Section: Biogenetische üBerlegungenunclassified

Alles begann mit einem Irrtum: Die Nomofungin/Communesin‐Story

2008

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Die Communesin/Nomofungin/Perophoramidin‐Story ist ein eindrucksvolles Beispiel dafür, wie biogenetische Überlegungen falsche Strukturzuordnungen korrigieren und Synthesechemiker zu neuen fruchtbaren Überlegungen inspirieren können. Nach intensiven Bemühungen anderer Arbeitsgruppen, die in der Totalsynthese von Perophoramidin durch Funk im Jahr 2004 gipfelten, gelang Qin et al. 2007 die erste Totalsynthese eines Communesins.

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An experimental strategy towards optimising directed biosynthesis of communesin analogues by Penicillium marinum in submerged fermentation

Cited by 15 publications

References 7 publications

Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids

Elucidation of the Concise Biosynthetic Pathway of the Communesin Indole Alkaloids

It All Began with an Error: The Nomofungin/Communesin Story

Alles begann mit einem Irrtum: Die Nomofungin/Communesin‐Story

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