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Pogostol biosynthesis by the endophytic fungus Geniculosporium

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2014

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Schulz, Barbara
Dickschat, Jeroen S.

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ChemBioChem. Wiley. 2014, 15(16), pp. 2379-2383. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201402298

Zusammenfassung

Six 13C-labelled isotopomers of mevalonolactone were synthesised and used in feeding experiments with the endophytic fungus Geniculosporium. The high incorporation rates of 13C-label into a sesquiterpene that was found in headspace extracts of the fungus enabled unambiguous identification of this volatile as pogostol without the need for compound purification, simply by collecting the volatile fraction with a closed-loop stripping apparatus followed by direct 13C NMR analysis (CLSA-NMR). The feeding experiments also gave insights into the biosynthesis of pogostol, including stereochemical aspects of the terpene cyclisation reaction. The possible biological function of pogostol is discussed.

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540 Chemie

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ISO 690BARRA, Lena, Barbara SCHULZ, Jeroen S. DICKSCHAT, 2014. Pogostol biosynthesis by the endophytic fungus Geniculosporium. In: ChemBioChem. Wiley. 2014, 15(16), pp. 2379-2383. ISSN 1439-4227. eISSN 1439-7633. Available under: doi: 10.1002/cbic.201402298
BibTex
@article{Barra2014-11-03Pogos-57484,
  year={2014},
  doi={10.1002/cbic.201402298},
  title={Pogostol biosynthesis by the endophytic fungus Geniculosporium},
  number={16},
  volume={15},
  issn={1439-4227},
  journal={ChemBioChem},
  pages={2379--2383},
  author={Barra, Lena and Schulz, Barbara and Dickschat, Jeroen S.}
}
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    <dcterms:abstract xml:lang="eng">Six &lt;sup&gt;13&lt;/sup&gt;C-labelled isotopomers of mevalonolactone were synthesised and used in feeding experiments with the endophytic fungus Geniculosporium. The high incorporation rates of &lt;sup&gt;13&lt;/sup&gt;C-label into a sesquiterpene that was found in headspace extracts of the fungus enabled unambiguous identification of this volatile as pogostol without the need for compound purification, simply by collecting the volatile fraction with a closed-loop stripping apparatus followed by direct &lt;sup&gt;13&lt;/sup&gt;C NMR analysis (CLSA-NMR). The feeding experiments also gave insights into the biosynthesis of pogostol, including stereochemical aspects of the terpene cyclisation reaction. The possible biological function of pogostol is discussed.</dcterms:abstract>
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