Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy
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Angewandte Chemie International Edition. Wiley-Blackwell. 2015, 54(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765
Zusammenfassung
Feeding of (2,3,4,5,6-13C5)mevalonolactone to the fungus Hypomyces odoratus resulted in a completely labeled sesquiterpene ether. The connectivity of the carbon atoms was easily deduced from a 13C,13C COSY spectrum, revealing a structure that was different from the previously reported structure of hypodoratoxide, even though the reported 13C NMR data matched. A structural revision of hypodoratoxide is thus presented. Its absolute configuration was tentatively assigned from its co-metabolite cis-dihydroagarofuran. Its biosynthesis was investigated by feeding of (3-13C)- and (4,6-13C2)mevalonolactone, which gave insights into the complex rearrangement of the carbon skeleton during terpene cyclization by analysis of the 13C,13C couplings.
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BARRA, Lena, Kerstin IBROM, Jeroen S. DICKSCHAT, 2015. Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by 13C,13C COSY NMR Spectroscopy. In: Angewandte Chemie International Edition. Wiley-Blackwell. 2015, 54(22), pp. 6637-6640. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201501765BibTex
@article{Barra2015-05-26Struc-57617,
year={2015},
doi={10.1002/anie.201501765},
title={Structural Revision and Elucidation of the Biosynthesis of Hypodoratoxide by <sup>13</sup>C,<sup>13</sup>C COSY NMR Spectroscopy},
number={22},
volume={54},
issn={1433-7851},
journal={Angewandte Chemie International Edition},
pages={6637--6640},
author={Barra, Lena and Ibrom, Kerstin and Dickschat, Jeroen S.}
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<dcterms:abstract xml:lang="eng">Feeding of (2,3,4,5,6-<sup>13</sup>C<sub>5</sub>)mevalonolactone to the fungus Hypomyces odoratus resulted in a completely labeled sesquiterpene ether. The connectivity of the carbon atoms was easily deduced from a <sup>13</sup>C,<sup>13</sup>C COSY spectrum, revealing a structure that was different from the previously reported structure of hypodoratoxide, even though the reported 13C NMR data matched. A structural revision of hypodoratoxide is thus presented. Its absolute configuration was tentatively assigned from its co-metabolite cis-dihydroagarofuran. Its biosynthesis was investigated by feeding of (3-<sup>13</sup>C)- and (4,6-<sup>13</sup>C<sub>2</sub>)mevalonolactone, which gave insights into the complex rearrangement of the carbon skeleton during terpene cyclization by analysis of the <sup>13</sup>C,<sup>13</sup>C couplings.</dcterms:abstract>
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